I’ve landed in Portland, a place where there is an abundance of Tibetan prayer flags (but no Tibetan people to be found), a surplus of people wearing deodorant that does not contain aluminum, and way too many culturally appropriated white dreads.
That said, I don’t mind it! Portland was just as easy to figure out as Chicago. In short, Chicago is Brooklyn. Portland is what would happen if Denver and Asheville had a baby. As much as I loathed Asheville (and the dating here is just as bad, if not worse), I liked Denver so it all evens out. I kinda feel about Portland the way I feel about Austin—the dating scene is severely lacking (toxic, even), but besides that, it’s not a bad place to live.
I’ve also already accepted that I’m not going on dates with any Portland men because they’re all insufferable Sad Boys™ and I love myself. Things have been picking up a lot in terms of freelance—I have 3 essays due this week—so I decided to use these next few weeks in Portland to write. [This decision was made easier by the fact that I just had a bunch of fabulous sex in Chicago and then get to see my Denver sex friend next month. I’ll survive.]
But with the trip wrapping up soon (so soon!), I realized I had all these stories from the road that never made it into an “Eat, Drive, F*ck” post because they didn’t fit in anywhere. But they’re all stories I love to tell, so here they are. Some of my most ridiculous moments from the road.
I arrived in Austin a few days before my 30th birthday. And I celebrated the way any woman should celebrate: hooking up with a very recently retired NFL player.
I told this guy I had his picture, knew his full name, and had security cameras at my condo complex, so I felt okay with him just coming to my place (please be safe when hosting first dates or booty calls; make sure you get all this info, tell the person you have all this info, and ALWAYS TRUST YOUR GUT). I had a good feeling about this guy and he was totally cool with everything. And it turned out great! He comes over and he is very handsome—6’5” and, because he’s retired with nothing to do, all he does is go to the gym. This guy could easily blow my back out, he’s very pretty in the face, and, my favorite, he’s hilarious.
The thing I liked about him was the first thing he admitted to me is that he is very dumb. We smoke a bowl, Postmated some tacos (Taco Joint in Austin is really good), and out of nowhere, he sighs and says, “I would be really bad at Wheel of Fortune.” He came out with a bunch of other winners like when I asked what he wanted to drink and he replied, “Water. I’m a real waterhead.” I don’t even know what that means, you guys.
Because he was 6’5” and built like Big Foot, he kept knocking over shit in my apartment. I was dying laughing the entire night.
“I don’t think you’re dumb at all, honestly. Because you’re funny,” I told him. “You have to be smart in order to be funny.”
“No, you don’t understand,” he said. “Dana, I went to one of the worst colleges in America.”
After dinner, I was cleaning up and he cornered me in my kitchen, pretending he was trying to get around me to throw something out. “Don’t do that,” I told him. “It’s very intimidating to have a 6’5” man standing this close to me, towering over me in my kitchen. If you want to kiss me, you have to ask.” I wasn’t annoyed because I knew what he was trying to do and I definitely wanted to kiss him, too, but I had to lay down the rules nonetheless.
He sincerely apologized before saying, “Now that I think of it, if I had a 7’5” guy coming toward me, trying to kiss me, I’d be intimidated, too.”
I am a sucker for people who can make me laugh. I walked him over to my bed.
We were making out and he had his hands down my pants when I realized, oh shit, I never asked him about testing. So I pulled away and asked if he’d been tested within the last 6 months.
“Oh…” he said, his face dropping. “We… don’t really do that here.” (Welcome to Austin, y’all. This was so common with the dudes I had met there and why I only slept with women from there on out.)
To his credit, instead of pressuring me to hook up, he asked if he should leave.
“Oh!” I exclaimed. “Just because I don’t feel comfortable having penetrative or oral, it doesn’t mean we can’t do other things!” I reminded him I’m a sex writer and we could get creative! He was down.
Cut to me naked and draped across this behemoth’s lap while he spanked and fingered me. If I remember correctly, I’m pretty sure I came three times. Then I got some lube and jacked him off while we made out. He. Came. So. Much.
See? It’s easy to have fulfilling sexual interactions that are outside the “norm” of what sex looks like (I hate saying that because there is no fuckin’ norm). Getting spanked and fingered for hours even felt more intimate than him just getting on top of me and having some missionary action. All parties were left satisfied. It was a fabulous early 30th birthday present.
A few weeks later, I was cleaning and realized there was some of his cum on the gravity blanket I have on top of my bed. I own a weighted sleep blanket because, you know, I’m an Italian greyhound during a thunderstorm.
Being the idiot I am, I tweeted about this.
Five days later, I got this email:
I have never cackled so loudly upon reading an email. Because wtf did Gravity blanket think happened? Do they employ a serial masturbator and this isn’t the first time he’s jacked off on a blanket? What is going on at that factory where it’s a jizz free-for-all?
I sent back the following email because I believe the truth will set you free.
That's right. I'm a fucking athlete.
I posted the interaction on my social media and the fucking bosses over at Gravity Blanket’s biggest competitor slid into my DMs.
I couldn’t believe this was happening. But, just like my sex toy collection worth close to $3,000 would tell you, I never say no to free stuff. And I knew my brother was thinking about getting a weighted blanket because we’re all terrible sleepers in my family.
And that’s how my brother got a free blanket.
As a former dancer whose rheumatologist once referred to her joints as "incredibly loose and flexible," I'm essentially a walking marionette puppet. I have a problem with hyperextension all the time. It’s bad because since I have double-jointed hips and shoulders, I never feel it when I’m doing it. At one yoga class in Asheville, I clearly fucked up and ultimately developed two golf ball-sized lumps on my lower back.
I was in so much pain I felt it even when I smoked some of my strongest weed. I couldn’t sleep.
The thing about Asheville is it’s so small that there aren’t many massage places and the ones that do exist are often fully booked up as a result of the scarcity. But even then, a massage would help to alleviate some of the pain, but what I really needed was bodywork—massage that incorporates trigger points to stop your muscles from spasming.
After hanging up with my fifth massage place who told me they couldn’t fit me in in the near future, I stayed in bed because the shooting pain in my legs made it hard to walk and started mindlessly swiping on Tinder. And that’s where I found someone who said they’re a licensed massage therapist in his bio. I almost cried when we matched.
HEY, I messaged him. I FUCKED UP MY BACK AND REALLY NEED YOUR HELP.
He asked if I was being serious. He asked, for clarity, if this was purely a transactional, platonic thing. I answered yes to both. He almost lost me when he asked if I wanted to come to his studio that he runs out of his house, but when I said I didn’t feel comfortable doing that, he said no worries, he could come to me and bring his table for an extra $10. I would have paid a thousand at that point.
I lived with my Airbnb host at the time and she works from home, so I felt totally safe inviting him over. He had also volunteered his license number so I could look him up and confirm that he’s never had any complaints filed against him (which was true—he hadn’t). When he showed up, he looked incredibly professional in slacks and a button-down shirt. I told my host what was going on—because LOL a strange man shows up with a massage table—and it was totally fine.
He gave me a massage in my bedroom with the door open. “Wow, this is really bad,” he told me after pressing on the lumps on either side of my spine. “You’re so lucky you found me because I’m the only masseuse in Asheville who does bodywork.” I silently thanked the Universe when, after an hour, he almost completely fixed my fucking back. The next day, it was 90% better. I was floored.
I texted him and asked if I could have one more session before I took my flight home; I feared sitting for hours in a cramped airplane seat would flare up the spasms in my back. He told me if I came to his home studio, he has a hot tub that he asks clients to sit in for a half hour before the massage because it results in more effective pain relief.
I told him since I was staying in Asheville during the winter for 5 weeks, I hadn’t packed a bathing suit. He said he wouldn’t want me to wear one anyway because the chemicals used to wash bathing suits are bad for the hot tub. Plus, I’d be in the room alone, so I didn’t need to feel weird about it. He said if I wanted to listen to any music while I was waiting out my 30 minutes, he’d set up Spotify on his sound system so I wouldn’t be bored. I sent him one of my favorite albums.
A few days later, I took a Lyft to his place and it was obviously legit. He had a room set up in his house with his table, there were plastic sandals and a robe for me to change into. Downstairs, in a renovated garage, was the hot tub. He set up the music, set a timer for a half hour, and left, closing the door behind him.
After about ten minutes, I started laughing. I was swimming around naked in the hot tub of a stranger I met off of Tinder, in a fucking basement, belting Etta James’ greatest hits. There have been a few times on this trip where I’ve been like, how did I end up here, and this was one of those times.
When I got back from Hawaii, I was fucking bummed. What made it worse was one day I woke up with another ruptured ovarian cyst. This is something that had derailed my time during my first leg of the trip in Boston, where I ended up being hospitalized.
I had bought expensive tickets to the symphony and really needed the distraction from my post-vacation blues. And I didn’t want this cyst to fuck up my trip the way it did in Boston, so I did a kinda stupid thing. And by kinda, I mean very.
When I land in a new city that doesn’t have legal weed, the first thing I do is put on all my dating app profiles “420-friendly cough I’m new here cough help a sister out cough wow I must be coming down with something.” Soon after I arrived in Austin, I met up with a rugby player at a coffee shop. He had asked me what I wanted and my answer was “Gorilla Glue and an indica so strong it will knock me on my ass.”
This idiot handed me both in identical, unlabeled plastic bags. So when I smoked up right after I had called my Lyft to the symphony, I thought I had smoked the Gorilla Glue, a light, giggly hybrid.
Narrator voice: That was not what I had smoked.
At first, I was like oh shit, but then I gave myself a pep talk. I was like, “All right, Hamilton. This will be fine. All you have to do is get into the Lyft, it will take you right to the symphony, and you will walk right in. That’s all you’re responsible for. Easy peasy.”
But when I was dropped off, the venue was nowhere to be found. It turned out the address on my ticket was the address of the box office, which was in a really bad part of Austin. There were lots of people walking around, talking to themselves. It was also 8 at night, dark out, and I could barely keep my eyes open. I was high as shit. The last time I was this high on an indica, I was at the Seattle airport, where putting cream cheese on a bagel felt like open heart surgery.
I kept looking on my ticket for the correct address, but the only one listed was for that damn box office. I was pissed that I had to admit defeat and take a Lyft home. But when I looked at the app, I saw a car wouldn’t be able to get to me for 5 minutes. The area I was in was so bad I didn’t feel comfortable waiting for that long there.
That’s when I saw a police car doing surveillance across the street.
I knew they’d know I’d be high—they’re fucking cops for chrissakes—but I decided to take the chance. If there’s anything Dana Hamilton is not, it’s a QUITTER. I was determined to get my ass to that symphony.
I jauntily jogged over and waved at the police officers (god, I was high). The one in the passenger’s seat rolled down her window. I knew I could play up the fact that I wasn’t from there and got lost on my way to the symphony. I had a New York license and my ticket to prove both of those facts.
I was too high to conjure up tears, but I made my voice crack as I explained the situation. “I don’t know where to go!” I said mournfully.
“Do you know what they’re playing?” the female cop asked. Thank god I remembered they were playing Beethoven’s Fifth as part of their program. Once she did a quick Google search, she found it. She turned to the cop in the driver’s seat. “It’s at the Long Center,” she told him.
He looked at me. “Ma’am. You have two options.”
I braced myself.
“You can either call a cab to come here and we’ll tell them the address or, if you don’t mind riding in the back of a police car…”
He didn’t have to finish before my dumb ass hopped into the back.
Fun fact about police cars: the back doesn’t have any cushions. It’s just hard metal.
The other cop asked to hold my purse because she had to check for weapons in it and thank GOD I had just taken all the weed and paraphernalia out of my bag the day before. I had been walking around with two baggies of weed in there for about a week because I just plumb forgot after buying from that rugby player.
On the drive over, the female cop kept asking me questions, which I hated answering because I was the kind of high where I wasn’t sure of the volume of my own voice.
“Where are you originally from?” she asked.
“NEW YORK I DROVE HERE ACTUALLY HEH HEH I LIKE AUSTIN SO FAR CAN’T BELIEVE I GOT LOST”
There was no fucking way they didn’t know I was high.
When we got to the symphony—which, mind you, was a 15-minute drive away, so I never would have found it—there was a long line of cars, so the cops asked if I didn’t mind hopping out right there and walking up the small hill to the symphony. I thanked them profusely (which was still probably me shouting) and walked inside.
When I got to my seat, I texted my friends “Just rode in the back of a cop car. Will explain later” before putting my plane on airplane mode since the performance was about to start. After it was over, it was fun when I turned my phone back on and essentially received many texts demanding what the fuck I just said. Now sober-ish, I realized something. There were definitely people in that line of cars that saw a woman exit the back of a cop car and walk directly into the symphony.
If you have ever believed that white privilege doesn’t exist, please remember that I once approached law enforcement high off my ass and was given a courtesy ride.
The only “bad” date I had in Chicago was with a guy who lived TWO BLOCKS FROM ME in Astoria when we both lived there. I’m putting “bad” in quotes because I had a great time
Now outside of my trip to Hawaii, I drink maybe 5-6x/year and when I do, my absolute limit is 2. Because I drink so infrequently, I usually tell people on dating apps I don’t drink because EVERYONE wants to meet for a drink. So this New York guy asks me out to dinner at some fancy French bistro. I say sure.
We’d talked on the phone a few times and it was fun chatting with him. He made a reservation for 8:30 and asked if we could meet at 7 to take a walk around the city. He said he’d pick a landmark near the bistro for us to meet at. I knew something was off when he texted around 6:30 saying he was already at a bar across the street from the restaurant. But whatever, I thought to myself, a landmark is a landmark. I ask if I should come over now and he says yes.
I show up fifteen minutes later and this man is VISIBLY hungover. I’m talking flushed to the point of being red-faced and he is sweating profusely. He’s also just finished a drink and when I walk up, I catch him ordering another.
This guy didn’t know why I didn’t drink; he never asked. For all he knew, I could have been sober. I was so floored by him thinking this was acceptable behavior (regardless of whether I was sober or not), that I was like okay, this is not going to go anywhere because what he did was so fucking rude... I might as well mess with the guy and entertain myself.
I pop a small edible and tell him we’re going to Portillo’s. Portillo’s is essentially the exact opposite of a fancy French bistro. It’s like what would happen if a hot dog stand fucked the 3-story TGIFridays in Time Square and I love it.
It’s a twenty-minute walk and by the time we get there, I am comfortably and mildly stoned. This motherfucker wants to get a drink. At Portillo’s. After I stare at him incredulously, I tell him if he wants to have a drink, it has to be a strawberry daquiri or else I’m leaving. He fights me on it, but in the end, he’s sucking down the contents of a boozy, frozen hummingbird feeder. I’m enjoying a chocolate cake shake (a vanilla milkshake with a slice of chocolate cake BLENDED INTO IT—amazing) happy as a pig in shit.
When I’m on a bad date and know it’s going nowhere, I ask deeply personal questions to make myself laugh. “How many times a week do you jack off?” is a known favorite. This guy is so drunk, he admits to me that he’s cheated on everyone he’s ever dated and still hooks up with his ex who is engaged to another person. I am eating all of this up (including a hot dog and French fries).
At the end of the “date,” which only lasted an hour, he asks if I want to come hang out with his friends at a bar and I tell him I’m going to walk home. “Ah shit,” he says. “I fucked up, didn’t I? I’m never going to see you again, am I?”
I double over laughing on the street. I’m still a little stoned and there are literal tears in my eyes. “You show up violently hungover and tell me you’re a cheater. What the fuck do you think?” I walk home and continue to laugh to myself. I can’t even call the date bad because at the end of the day, the guy never said anything rude to me, I had some company while I ate dinner, and I didn’t invest much of my time. I took it for what it was and it still makes me laugh when I think about it.
Like I always say: I don’t have bad dates, just good stories.
The day I left Chicago, I went to the apartment of the man I wrote about in my last post. I spent my remaining three hours getting devoured like he was on death row and requested my pussy and ass as his last meal. I tend to lose track of time when I hook up with this person, so we set an alarm to ensure I’d get a car to the airport on time, but when it went off, I said, “Two more minutes.”
That’s how I feel about Chicago as a whole. I just wanted two more minutes. I really, really didn’t want to leave.
My friend and I were a little nervous about me getting to the airport because my Lyft driver took a solid ten minutes circling the block trying to find us. Once she picked me up, she then proceeded to tell me look out the window because “isn’t that baby so pretty!”, didn’t know if New York City was on the east or west coast, and asked why Chicago sex friend wasn’t coming with me. I texted him this and told him next time, if given the option, I’d pack his mouth in my carry-on because I know what it do. [insert tongue emoji a thousand times]
I adored Chicago. I… liked it better than Boston, which is saying something. I’m still moving to Boston at the end of the trip, but if it wasn’t so far from my friends and family, I’d sign a lease in Chicago in a heartbeat.
I lived my best life there. I stayed in a gorgeous (and very expensive, but worth it!) 3-story townhouse with a roof I ate lunch on every day. I got Classpass and found my love for Pilates again. I ate at many of the best restaurants in the city, wrote at the best cafes, walked around and shopped in the best neighborhoods, hit up the beaches, and went on dates with some fabulous people. I can’t recommend spending 6 weeks in Chicago during the summer enough.
Let’s break it down, once again, into my blog’s namesake, shall we?
I ate a lot here. Chicago is an incredible eating city; nothing will ever top Austin, but I could almost argue Chicago’s on the same level. I didn’t have a single mediocre or disappointing meal here. I also didn’t cook here… at all. I went out for every dang meal.
Gilt Bar: The cacio e pepe… oh my GOD. Get it and the chocolate cream pie.
Honey Butter Chicken: Fuckin’ fantastic. After 5 weeks in Asheville, I vowed to never eat pimento cheese EVER AGAIN, but their pimento mac and cheese was divine.
Bad Hunter: If you go here and don’t get the potato fry bread (with burrata and cherries), I’m pretty sure you’ll get arrested. The menu is seasonal (though I think the fry bread is a staple), but if they still have it, get the beef kabob on polenta, too. Great mocktails, too.
Little Goat Diner: Get the crudité platter (it comes with homemade naan with everything seasoning on it) and the “One Twisted Sundae.” The latter is a fudge brownie topped with pretzel-flavored ice cream, caramel sauce, whipped cream, and pretzel pieces. It was divine. I came back and got the turkey club, which was so damn good and, remember, I’ve tried the best delis in NY and Boston.
Clever Rabbit: My friend told me their burger was “stupid good” and she was right. Best burger I’ve eaten in my life.
El Metro Cantina: These tacos are better than the ones I had in Austin. Get the chicken tinga and the pork. Their red and green salsas are legit.
High Five Ramen: Get there early (like 4-4:30pm). The wait can get up to 4 hours and it’s a twelve-seat establishment. Get the classic ramen, half-spice. It was delectable.
The Violet Hour: Really cool speakeasy in Wicker Park. I love how it’s designed. Strong drinks.
Café Baba Reeba: I usually don’t go for tapas places, but everything on this menu was delicious. I loved the fried chicken thighs, beef kabob, stuffed mushrooms, and burrata. I enjoyed this place so much and couldn’t make it there during a week I was on deadline, so I had it delivered. I ordered the chicken and mushrooms again, as well as their garlic potato salad and Brussel sprout and manchego salad. Incredible.
Gyu Kaku: There are a few of these across the country and when I’m back in NY, I will *absolutely* be hitting it up. I love Japanese barbecue, but sometimes it can get expensive. This place was very reasonably priced and all the food was delicious. Get the jelly sake. It’s so weird and yummy.
Stan’s Donuts: Classic glazed is where it’s at. Game over.
Sawada Coffee: Their black camo latte made me see God. It’s matcha and espresso, which, yes, I KNOW it sounds disgusting, but it turns out it’s DELICIOUS and tastes like chocolate. Get it with almond milk instead of regular milk. Just trust me.
3 Arts Café: Chicago sex friend recommended this place and holy shit. It is my dream place to write. I thanked him profusely. (Get their fries with garlic aoli and their warm chocolate chip cookie + a cup of coffee. Yes, I am aware that I eat like a raccoon.)
Beaches: I tried going to Oak Street beach, but it was closed for an event, so I walked 15-min north to Long Avenue Beach. I was warned by a friend that it would be crazy busy and, yep, it was. But I enjoyed it nonetheless. I liked Kathy Osterman Beach much more. It’s a little bit of a hike and is nicknamed “the gay beach,” so, out of respect, I shamelessly flirted with a very attractive woman while wading up to my waist in the FREEZING COLD water (and got her number).
Movie theaters: I took the blue line to Logan Theater and enjoyed this super cute place until the film “Eighth Grade” DESTROYED ME. I also went to a “Clueless” shout-along (where the audience all quotes the dialogue together) at The Davis Theater with my friends and it was fabulous. The theater was gorgeous.
Workouts: I highly recommend Ascend for their classic reformer class with an instructor named Sheridan; she’s a sweetie. I also like Pilates Pro Works’ machine classes if you want a challenge. If you like aerial silks, Air is fabulous. Challenging, but incredibly fun.
Wicker Park shopping: Wicker Park is a very cute area. It’s essentially the NYC East Village equivalent. I went to Penelope’s—a super affordable option—and bought a cute lil’ cotton off-the-shoulder black romper that makes me feel like Audrey Hepburn if she was into toddler cosplay. I also went to Una Mae’s (slightly more expensive) and bought a delicious white cotton shirt and long, dark navy bodycon dress. But my favorite shop was Moon Voyage (very pricey, unfortunately), where I impulse bought an expensive slinky black dress for absolutely zero reason (I’ve been dying to find a dress like this for years though) and this light pink silk tie-front top.
I wore that shirt to coffee with Chicago sex friend and he told me it was very distracting. I told him it was payback for him sales technique-ing me. :)
When I first got to Chicago, as I’ve mentioned in previous posts, I went on a date with a 24yo for the first time in my life. I’m a 30yo woman who, all throughout her twenties—with the exception of someone who was 26 when I met him—dated older, this was an experience that made me laugh at myself. But, as I’ve written earlier, he was great. Incredibly intelligent and eloquent and a total cutie. But our schedules just didn’t sync and we fell out of touch. No harm, no foul. He was cool.
Next, I went out with someone hilarious, but there was no sexual or romantic spark for either of us. I did want to hang out again as friends, but, alas, I couldn’t find the time. He was cool, too.
Then I went on a date with a super adorable woman in an open marriage who I really liked! She did pole-dancing and I really wanted to go to a class with her, but then she had a family emergency… and then my job got crazy… then I got strep throat… and our schedules didn’t mesh. I felt horrible because I truly did want to hang out again—I wasn’t trying to pull a slow fade or anything—and I actually did want to redeem the “one free threesome” coupon she kindly offered to me on behalf of her and her hot ass husband, but, AGAIN, it just didn’t work.
About three weeks before I left Chicago, I met the gorgeous dude from my last post who I ended up hanging out with for the rest of my time here.
I do not regret this choice.
In all, everyone was fabulous! The Chicago dating scene is great! I only went on one “bad” date, which I’ve written about in the next post. And it wasn’t even bad because I thought it was hilarious.
Chicago, you are tied for first place with Boston. Not sure how that happened, but you are. I rerouted my drive home to return for a few weeks next month. Maybe I’ll be living there permanently in a few years… Who knows.
Two Fridays ago, I texted my group chat with two really good friends like I always do. We all live in different states and text every day. That morning, I told them I had a really good date. “I’m exhausted because we didn’t get to bed until 3:30,” I told them.
“I’m sorry, did you just say we?” one of them asked in a voice note. “As in… you let someone sleep over?”
“WE ALSO CUDDLED,” I admitted. “I DON’T KNOW WHO I AM ANYMORE.”
The truth is he was incredibly kind (and didn’t snore), I felt horrible making this sweet man take a car home past 3am, and he said he wanted to eat my ass in the morning. I mean… how could I say no when breakfast is the most important meal of the day?
Taking my own damn advice from my last post served me well. My week off from dating was the perfect reset button. Once I spent a week devoted solely to taking care of myself, I was able to hop back into it with a positive attitude. I found the fun again. Because if dating isn’t fun for you, you probably shouldn’t be doing it. Circling back when you feel better is important because the experiences you have will be ten times better than if you force yourself to date while feeling shitty.
Cut to the Thursday night after my week-long break. I had a good feeling about this guy before we met because he laughed at my silly jokes and spoke very intelligently about misogyny—and not in the showboat-y kinda way men who very loudly declare they’re feminists do. I'd told him about how I recently had to set some idiot’s ass straight after he claimed friendzoning is a thing. (I actually wrote something for Cosmo a few years ago about why it’s not.) I sent him screenshots of the conversation and afterwards he texted, “That was exhausting. I don’t know how you kept talking to that guy.”
After he said that, I put my phone down, went into the bathroom and proceeded to bonsai my bush into a cute upside-down triangle before the date. Yanno. Because I respected him so much.
I also knew he worked in Sales, an industry requires a certain personality type. You have to be ambitious, an excellent conversationalist and a fairly extroverted people person to do well in that particular career path. I’m someone who values social adeptness and emotional intelligence above all else when determining who I want to spend my time with. Plus, this dude was a Leo. A Leo who works in Sales meant this date wasn’t going to be boring at all.
We met at an amazing tapas place called Baba Reeba (so, so delicious) and I experienced two unexpected firsts:
Y’all also know how hot HB, the only decent man I met in Asheville, is:
And I’ll just say my Denver sex friend has an overall appearance just as impressive as his dick, which earned him this coveted award from me:
I wasn't intimidated by any of those men.
But when I met up with this date at the foyer of Baba Reeba, it was the first time I ever felt like someone was waaaay out of my league. I already knew he was going to be hot because of his pictures on Tinder, but when I saw him in the flesh, I was like oh fuck. This is not going to bode well for me. That’s the God’s honest truth.
He looked better than his pictures, and I’m not sure what kind of witchcraft made that possible. This kid looked like a brunette, bearded Zack Morris who powerlifts and models when he’s not at Bayside chopping lumber in the back of the school. I was thrown off my game. I didn’t feel self-conscious per se, just realistic—something along the lines of if this guy doesn’t want to go home with me, I wouldn’t be surprised. Not a reflection of me or my self-worth, but just like… I get it.
2. He is as direct as I am when it comes to communication.
I’ll admit #1 was stupid for me to think because this man knew exactly what I looked like. It’s not like I arrived and appeared vastly different from my pictures or videos. I was still intimidated though. When I’m intimidated, I’m not my usual, painfully direct self who says stuff like “So this was fun. Do you want to fuck around now?” when the bill comes.
My assumption that this date would end with an attempted half hug (that’d I’d pull into a REAL hug because I’m not a QUITTER) and vague promises to hang out again was strengthened when my date suggested a unique Chicago thing to do, I said “I’d love to!” and his response was “maybe you could go with a friend.” My pussy essentially sat down in a director’s chair and shouted THAT’S A WRAP into an old timey microphone.
Sex was clearly off the table, but I was like hey, I’m still going to enjoy this date. We ate some mind-meltingly good food and talked. He was clearly very intelligent, a good storyteller, and very kind. And then, before I knew it, the place was packing up. That’s odd, I thought to myself. We had only met at 7, but some places in Chicago close on the earlier side, so I brushed it off. My date then excused himself to use the restroom and looked at my phone. It was 10:30.
The best part of the date wasn’t the fact I was having such a nice time that three and a half hours flew by. The best part occurred about mid-date, when this man looked over at me and said, “I assume you want to see me again,” which is the boldest, ballsiest, most Leo thing I've ever witnessed. I scream-laughed. “I can’t believe you just said that!”
Now here’s the thing. If someone said that to me and they were wrong, I would give them more crap than a Port-A-Potty at a chili festival. But he was 100% right. I did want to see him again. And he could tell I did.
That is some shit I would pull. I’ve been on dates where people have told me I’m “refreshing” to talk to and they're having a lot of fun and my response has been “Well, of course you are because I’m great.” Now I felt like I was on a date with myself.
The tables had fuckin’ turned. This man had major BDE (Big Dana Energy), so I didn’t pull any of my usual tricks. Right before we left the restaurant, I asked what he wanted to do so that if he preferred to end the night, he had an out. When he told me there was a place close by with a cool rooftop, I was like okay, he wants to continue this, but I still couldn’t tell if that was the extent of it. After all, this guy was so damn polite, he told a story at dinner about how he was once catfished, stayed, and asked the person if they wanted to have a drink.
THAT IS HOW KIND THIS FUCKER IS.
So I still didn’t directly ask if he wanted to fuck, opting instead to tell him my townhouse has a private roof deck with a great view of the city. When he agreed to come back to mine and put his hand on my bare knee during the Lyft ride over, I was like okay, Dana. You no longer need to be in disbelief that this hot man is interested in fucking you. It’s a possibility, Hamilton.
In the car, I told him I was surprised he still wanted to hang after he suggested me going off and doing something with a friend earlier on in the night. He then told me he was doing something he does at work called “keeping behind the pendulum,” a tactic used to show clients you’re not too eager too early on in an interaction.
He fucking sales techniqued me.
“Listen,” I told him. “I know you don’t believe in this stuff, but… that was the most Leo move of all time.”
We got to my place and I showed him the roof deck, but I was only wearing a silk dress and it was chilly out, so we went inside after a few minutes. It was only when we were both sitting on my bed that I asked if he wanted to fuck me. He said he did. I admitted that under any other circumstances, I very directly tell people I want to fuck them. I didn’t with him because I truly couldn’t tell.
He then reminded me that I had asked him to come home with me and the moment we came inside from the roof deck, I put my hair up.
Touché, friend. Touché.
After we established mutual emphatic consent, we still kept talking because we liked chatting with each other! But eventually I told him we had to stop because I really wanted his clothes off. There’s that direct Dana Hamilton communication we all know and love. We stopped talking.
Sometimes, inexplicably, there are people who are so in tune with their partner’s body--even during sex on the first date!--they will start doing what the other person wants just as they open their mouth to say it.
“S—” was all I’d manage to get out before he’d spank me. The last time I experienced this kind of sexual ESP was a hookup in Williamsburg three years ago whose birthday present to me was a floral bouquet with lots of peonies in it and four hours of oral sex.
Speaking of spanking, this dude was a pro and I told him that. Most people hit way too hard (like they don’t understand I’m an actual human person and not a meat sack) or way too soft (like their hand is dead at the wrist). Some hit too high, near the lower back, which neither feels good or makes a satisfying sound. But I had to give this guy zero direction. “It’s an art and a science,” he explained later and I cackled.
There was also a moment during the hookup where I was kinda floored by how good at sex this guy was and then remembered how competitive he is. Former football player, current powerlifter, works in Sales... I was like huh. I like competitive men. Because, to them, getting me to come is like scoring points in a game and I want my sex life to be a damn pep rally.
[I know that analogy doesn’t make sense because you don’t score points at a pep rally, but I DON’T KNOW SPORTS STUFF, ALL RIGHT?]
Four orgasms and one 69 session later (usually one of my least favorite positions because trying to focus on blowing a guy while they’re doing an excellent job of eating your pussy is like trying to take the SATs with a pencil covered in bees), my Chicago date and I kept trying to go to bed, but couldn’t stop making out. Hooking up with a good kisser is a goddamn treat; if someone’s good at kissing, I don’t want to stop kissing them. Bad kissers frustrate me because they turn me into a bad kisser, which I know I’m not. Kissing is a dance. If the person you’re dancing with is a bad leader, you start tripping over your feet. I can’t tell you how many men have attempted to waltz with me and made me look like that recent video of Lindsey Lohan where she appears to be doing a solo audition for the Greek Rockettes and no one is watching.
We finally went to bed at 3:30am and I woke up a few hours later for my day job. Having your ass eaten in the morning is a risky move because sometimes morning tummies are gurgle-y. I had also had a few glasses of sangria at the tapas place and never drink. Keep it together, Hamilton, I told my asshole during my quick shower. My GI tract, after being alerted by my brain how hot this dude was, cooperated. “Don’t ruin this for her,” my stomach told my butt. After returning to bed, this handsome gentleman gifted me another two orgasms by eating my ass like it was two honey-baked hams and he had just given up on keeping kosher. I then clocked into work and pounded some cold brew with him before he called a car right before my daily morning video meeting with my department.
Five minutes after he left, I received a text message containing the sentence "I clearly want to see you again.”
^^ What a great ending line to this piece that would be. But this is not where this story ends.
A few days later, I mentioned I had written this post. Though I had written about him completely anonymously (no name, image, or identifying personal info), it still somehow felt wrong posting it. After all, besides my post about my trip to Hawaii with Homeless Bryan (HB), whose blessing I received before and after I wrote it, there hasn’t been an entire “Eat, Drive, F*ck” post devoted entirely to someone I’ve met on the trip. It just felt weird.
“Wait, wait, wait. You wrote a blog post about me?” he texted. “Can I read it?”
I was hesitant. Because this guy would essentially be reading the equivalent of a Yelp review of his dick. Though I knew everything I had to say about him was incredibly positive, I tried to put myself in his shoes. Would I be freaked out if I read something like this a professional writer had written about me after a first date? I didn’t know. And the last thing I wanted was for this guy to run screaming for the hills when I was leaving Chicago in just a few short weeks and really wanted to see him again.
I’ve always said that if a man gets freaked out by me being exactly who I am, I shouldn’t be sleeping with them anyway.
But… I’m also a weak woman when it comes to beautiful men who eat me out like it's the Last Supper.
[Holds up bread] "This is my body." [Holds up wine] "This is my blood." [points to my pussy] "And this is my muffin."
Plus, I get it. It takes someone who is very secure in who they are (and respects what I do) to be excited about appearing in my writing. Lord knows not every man I've met has been like that. In fact, very few have been.
“Will you judge me for it?” I asked.
“Okay. Gimme your email address.”
[gives it to me] “Or you could just bring it with you when I see you Wednesday night.”
“Omg no” is what I typed back, but what was actually happening was me flailing on my bed going oh god oh god oh god that sounds horrible what the fuck am I gonna do with both my palms pressed to my forehead.
“I would be mortified,” I told him.
I couldn’t stand this charmer.
“I will quite literally sit on the ground, bent over, my face in my hands,” I told him. “You know. Like a real professional.”
“Could you be naked though?” he texted back.
He had found my Achilles heel.
“Ok you drive a hard bargain," I told him. "But I'm in.”
On Wednesday, after we met up at a speakeasy called The Violet Hour in Wicker Park (really cool place), he came back to mine, we fooled around, and afterwards, as promised, I let him read this post off my laptop while lying naked on my bed. Sitting there watching him read would make me curl up and die so I kept my hands busy by kneading the back of his thighs and calves with warm oil from a massage candle.
He laughed at all the appropriate places and complimented my use of memes. When he read my line about competitive people thinking bestowing orgasms is like putting points up on a scoreboard, he exclaimed, "That's exactly what it's like!" My anxiety subsided, and I was happy. The latter may have been due to the fact that my hands had traveled further up his legs and were now on his fantastic ass, but who’s to tell, really? Who's to tell?
“This is great!” he said before we made out for hours.
I let him stay over again. That Big Leo Energy will get ya every time.
When people tell me they hate dating, they’re tired of the slog, don’t feel like they’d be attractive to a potential partner, or are still hurting from a breakup, I don’t tell them “Be more positive!” or “Oh, you’re being silly. You’re great!” or “It’s time to move on!” Instead, I tell them, “Take a break.”
You know why? Apps are always going to be there. Pussy’s always going to be there. Dick’s always going to be there. There is no rush.
But everyone feels the pressure to be partnered, and it makes sense, right? If you’re partnered, you’re seen as “successful,” like you’ve unlocked some sort of achievement. If you’re single, there must be something wrong or you’re not trying hard enough. If you’re partnered, you’re better than your single friends. If you’re single, your goal should be to ultimately become partnered. It’s just like how we view bodies: if you’re attractive by society’s standards, you’re “good.” If you’re not, you “should” be working on achieving it. And the harder you work, the better you are. The more you’re worth.
“Work harder, be better” is what we’re told constantly.
I recently had to tell a fellow overachieving lady a hard truth: successful women often get frustrated by dating because in any other situation, we know that if we put a ton of effort into something, it will yield results. If you work hard in school or your career, you get a payoff. Dating doesn’t work like that. You can put in a ton of effort and nothing is guaranteed to you.
[Side tangent: One of the reasons we’ve been taught to worry about our attractiveness is because it’s associated with attracting the male gaze. One of the reasons we’ve been taught to worry about being partnered is because it’s associated with holding the male gaze. Annually, the beauty industry is worth $445 billion, the weight loss industry = $66 billion, and the wedding industry = $72 billion. Internalized misogyny and capitalism are a real bitch, y’all.]
The truth is there's no shame in being single and there's no shame in being celibate. I actually respect you a helluva lot more for focusing on yourself until you feel better (and feel better about dating) before you return to it than I do for continuing to date and have sex and being miserable. Plus, when you’re not feeling great, both the date and the sex is going to be bad anyway.
It’s okay to take a break from dating.
I will say, though, that I have a hard time following my own advice because I have the sex drive of a 15yo girl. (I know the conventional saying is “a 15yo boy,” but guess what? Teenage girls are just as horny as boys. It’s just that no one talks about it.)
The problem with having no stability as you travel from place to place is that… you have no stability. If you’ve been reading my blog for a while, you’ll see that I’ve experienced a lot of ups and downs. And when there’s no stability and you’re working 4 jobs, it can be very taxing on the mind.
Shortly after I arrived in Chicago, I started working straight through from 7am to 11pm. I didn’t get more than 4 ½ hours of sleep per night for a solid week and a half. I was falling into perfectionist tendencies and black-and-white thinking. I must date and talk to people on apps. I must be on social media for my job. I must follow through on all projects I promised myself I’d do outside of my day job (freelance, blogging for other companies, writing my book). I don’t have time to eat actual meals. My basic sex and food needs? Booty calls and takeout will have to suffice.
And then I crashed. Hard.
Last week, I crashed so badly, I only left my townhouse to shuffle down the street to the drugstore, buy some diet iced tea, and drink it in bed while looking at my phone for hours. I couldn’t relax. I was exhausted but wired. Eventually, I put my phone down and laid on my side, one arm over my pillow and the other under it so I could hug something while I half-slept, my cheek pressed to the cool fabric. My body was going into Bad Brain mode, something I only experience during extreme periods of stress. This is what was going through my head:
That's when the Universe was like "oh fuck OFF, Dana" and threw me a bone.
Before going to bed, I picked up my phone to set my alarm and saw a text from one of my closest friends in New York, Dave.
When I lived in NYC, I was at Dave’s apartment pretty much every other week. Dave’s heard every dating story I’ve ever had; many a tale has been told while we’ve eaten pepperoni and mushroom pizza with his dogs on our laps. I have the key to Dave’s apartment, which I offered to return to him before my year-long journey.
“Keep it,” he told me. “That way you know you always have a home here.”
Dave’s text was a request for my address in Chicago because, completely unprompted, he wanted to send me a gift. I smiled, the knot in my stomach loosening slightly, and went to bed. I slept eight hours for the first time in ten days.
When I woke up, I snapped out of it. My usual way of thinking came back to me: any “desire” to be thinner and partnered because I will be “better” because of it—complete bullshit. I’ve been miserable as a thinner person and miserable while in a relationship. My worth isn’t determined by my body being considered attractive to a man or the fact that a man has chosen me as his partner.
That afternoon, I FaceTimed Cecilia, my therapist extraordinaire. I told her about my friend Sophie’s suggestion—one that was given to me after I confessed I had noticed my hair falling out in clumps—to not do any work besides my 7am – 4pm day job for a full week. No freelance work, no research for my book, no work for the two companies I decided to partner with.
Cecilia agreed that it was an excellent first step. “What else can you do this week that you know will make you feel better?”
I blurted out the answer immediately. "Not date."
The truth was clear: I had become the exact type of person I encourage to take a break from dating. I hated it, though, because, like I said earlier, I am hornier than a rabbit... in a chatroom in 1995 with their mom’s credit card. I told her I really wanted to date, but knew it wasn’t a good idea right now.
Get yourself a therapist who, when you say, “If I don’t have sex in over a month, I start to go insane,” replies, “I get that.”
But taking a week off wasn’t going to kill me.
Cecilia's homework for me was to make a list of things I’d do this week to prioritize sleep, nutrition, and physical activity—three things I know improve my mental health.
I started to set two alarms: one at 9:30pm telling me to get ready for bed and one at 10pm telling me to go to bed. I ordered food with actual vegetables in it. I went to Pilates and aerial classes 4 days a week. I got out of the fucking house.
I hung out with my two friends in Chicago (an amazing couple I knew for a while on the internet who turned into real-life friends). They’re both incredibly kind, hilarious, and generous, and introduce me to the coolest, hippest restaurants in Chicago. Many of the most exclusive restaurants here are hidden and you have to be in the know to even be aware they exist. There have been plenty of times where I’ve shown up to where I *think* the restaurant is, only to text one of the pair, “I think I’m here? WHY IS EVERYTHING IN THIS CITY A SECRET”
The three of us went to High Five Ramen, a 12-seat ramen establishment not even open yet that somehow has an hours-long wait (we were at the front of the line, however, cuz my pal has connections). That same night, we got drunk and ordered McDonald’s (something I’ve never done in my life, believe it or not) from the corporate headquarters on Randolph Street, where you order from a touchscreen and can sample items from various international menus. I read an incredible book on my rooftop overlooking the Chicago skyline (video below), I got a pedicure, I put together a care package for my friend in New Zealand, I bought a card for my dad, I wrote this blog post (the only writing I do for me and not for money).
I also had a soul-nourishing hangout with my friend VP, who has visited me a few times while I've been on this trip. I always love seeing him. We’re both writers and we’re both comedians, so what the fuck do you think happened when we walked by a wig store with a “going out of business” sign in the window?
I also went to Bad Hunter on my own and did my favorite thing: sit at the bar, order a full 3-course meal, and sip a fancy mocktail while writing on my laptop. The next time you see someone eating alone and feel bad, I promise you they are enjoying every second of no one fucking talking to them while savoring their meal.
I took a day off from my day job, woke up when it felt good, got a latte at Sawada coffee (seriously, the best espresso I’ve ever had), shopped at the brand new Glossier pop-up shop around the corner, visited Warm Belly Bakery, and then went to… my favorite place on earth. I’m not exaggerating. Because there’s one in my home city.
My favorite place in New York City—even ahead of Veselka (Ukranian diner), Levain (the best fucking cookies you’ve ever had), and Van Leeuwen (I dream about their honeycomb ice cream)—is a place called Aire Ancient Baths. In the middle of nowhere, right next to Chinatown, is an underground spa the size of half a city block filled with hot pools, cold plunges, a salt float pool, and an aromatherapy steam room. Only six exist in the world: New York, Barcelona, Sevilla, Almeria, Vallromanes… and Chicago. How Aire Chicago existed before Aire London, Aire Copenhagen, or Aire Paris (all slated to open within the next two years) is beyond fuckin’ me, and I was floored when I found out there's one within walking distance of my Airbnb. If someone on Tinder hadn't told me, I never would have known.
Being at Aire Ancient Baths is one of the most relaxing experiences of your life. It’s even more relaxing after taking two edibles before you walk in.
When the 24yo I mentioned in my last post texted me asking if we could meet up on the Friday night of the week I promised to devote to myself, I suggested another day when all I truly wanted to do was bang him again.
You don’t have to wait until you’re perfect in order to date (because then you’ll never date!), but you do have to wait until you feel better.
I wanted to write this post to show that the self-love, sex-positive chick sometimes has bad body days. She also has to constantly create boundaries with herself and others. She gets dating fatigue, too. She gets tired as hell, too. She sometimes gets sad about cultural ideas surrounding relationships and dating and even falls victim to them sometimes. And that’s okay. She, like everyone else, just needs to hit the reset button sometimes.
I haven’t lived in Chicago for all that long, but the one thing I can say with complete certainty is that it is the easiest city to arrange a threesome. But we’ll get into that later.
The funny thing about Chicago is it wasn’t even on my original list of cities I wanted to try living in when I started planning the trip around this time last year (wow, that’s weird to think about). Bear in mind that at that time, I had never lived in a new city before in my entire life. I had picked cities at random that sounded interesting to me. I do recommend doing this, but I do not recommend doing this and not running it by friends who actually know the places you pick.
For example, Savannah (Georgia) was originally on my list until a very kind friend informed me that I would probably be murdered there.
“But it’s next to the beach!” I argued. “I love the beach!”
“Have you ever seen the movie Deliverance?” he retorted.
I crossed it off my list.
And then I kept hearing from people who have known me for a long, long time that they could picture me loving Chicago. I had to go during the summer, they insisted. I made it work.
When I landed in Chicago, I felt sick to my stomach. (I found out later that I had contracted E. coli.) I was vomiting, shitting my brains out, had a splitting headache, and a high fever. My third night in Chicago, I called my friend HB (Hawaiian Bryan from my last post) from the bathtub at midnight because my chills were so bad and enjoyed yet another story of him being the dumbest human alive (he fell out of a tent and rolled down a hill).
The best thing my therapist has ever said to me happened last year right after I had found myself single with nowhere to live and had come down with mono and Lyme’s: “The only thing that can get Dana Hamilton to slow down is her getting incredibly sick.”
Miserable in bed, I realized I may have too many irons in the fire. Over the last month, I’ve agreed to partner with both a sex toy seller and a Canadian condom company that I love (and y’all never heard of, but I will soon change that), met with my agent and figured out the premise of my next book (he wants me to write a proposal while in Chicago so he can shop it around this winter), committed to writing sex toy reviews on my site, continue to post on this blog weekly and continue to freelance. Oh, and I also have an 8-5 day day job in marketing. Beyond the E. coli, I was run down.
I took a little break from social media, a lot of hot baths with half a bag of eucalyptus Epsom salt dumped into ‘em, and 2 days off from my day job as pure evil flowed through every orifice of my body. I reminded myself that if I don’t do some serious self-care and take a break from some things, the book that I’m super passionate about will never get written. But I decided to stay on dating apps because, believe it or not, dating is my self-care. Let me explain.
One of my friends in LA spoke with one of our mutual single friends who had asked her how I maintain a positive attitude while dating. “I think Dana just loves people,” she told her.
It’s true. I fucking love people. Sure, sometimes people are pretty awful, but people can be fascinating, ridiculous, sweet, and humorous, too.
Being a writer with a remote day job is tough because both require you to spend long stretches of time alone. And I am a very extroverted people person. My day job and my dating life allow me to interact with the world around me. Writers need that. That’s why dating is self-care for me.
But dating in the Midwest is one of the most interesting experiences I’ve had on this trip so far. At first, it was very challenging, but then I got the hang of it.
I once told a hookup that the only time I’m not horny is when I’m very, very ill. But I guess that was a lie because even when I had pneumonia (you know, that illness where your lungs start to fill with fluid?) in high school and was weak and feeble as Old Rose™ in Titanic, I jacked off pretty every single one of those 30 days I was out of school. With this bout of E. coli, in the small stretches of time between each prayer for death I whispered into the sky as I laid dead-eyed on my bed, I was arranging dates and booty calls on apps for when I was feeling better. I hadn’t had sex in a month and was starting to unravel.
And that’s where I encountered my first road block.
Because I booty call women and date men, I separate my apps: Tinder is for women and OKCupid is for men. If I blend the two in any way, I get fetishized by men and looked at as "not as serious" by women.
I sometimes struggle with the label “bi” and prefer the term heteroflexible. Because I only fuck women when I’m horny and don’t want to deal with men’s bullshit. That’s the god’s honest truth.
These are real profiles I've encountered from men in Chicago:
Now don't get me wrong--I can very happily have sex with only men for the rest of my life. I love men. I crush on men. I fall in love with men. When I date a man and really like them, I think about ‘em. Women? Never. But do you see now why I sometimes like to fuck women?
I also just like eating pussy, you guys.
Because I was only looking for hookups (no strings, I never see you again, take care), I created an honest profile that said just that and was shocked by the amount of bites I had gotten. Because if I had that bio in NYC or Boston, the line to my apartment would be out the door.
But women don’t operate like that here.
For a solid few weeks, I was getting very few matches, which has never, ever, ever been my experience on Tinder. I was confused, but not disheartened. There is an ebb and flow when it comes to dating. By that time, I was feeling better anyway and wanted to make up for the week I lost sick in bed. I wandered around the River Walk, went shopping in Wicker Park, sampled incredible food at Gilt Bar, Clever Rabbit, Big Star, Windy City Café, Jerk, Piccolo Sogno, and Bombobar. I savored an incredible glazed donut from Stan’s and drank the best iced latte of my life at Sawada Coffee. I went to a shout-along of the movie Clueless (where the audience quotes all the dialogue together) at The Davis Theater with some friends. I enjoyed the roof deck of my incredible 3-story townhouse and read books in the sunshine. I found a great workout. I went to Up and Up at the Robey Hotel and took in gorgeous views of the city.
This is a reminder that when dating seems a little slow, it is the perfect time to go out and fucking enjoy yourself.
But I was still dying for a fun, hot hookup. My clit was pretty much tapping on a microphone, going, “Is this thing on?”
My Tinder bio was essentially the equivalent of “FREE PUSSY," so why did I have so few matches? I went out with an amazing long-time internet friend turned IRL Chicago friend and told her about THE CROSS I HAD TO BEAR. She looked at me, laughed, and said, “Welcome to the Midwest. Everyone here wants to get married.”
“But where are my fun lesbians at?” I whined.
“They’re looking for a wife,” she replied.
I realized I hadn’t “dated” women for all that long and was still learning the ropes. (I’m putting dating in quotes because dating right now is me asking someone if they want to come to my apartment, order takeout, smoke a bowl, and fuck around.)
Then I remembered one of my lesbian couple friends in NYC. They have promise rings that are made of silicone so they don’t have to take them off while they lift weights. If that’s not the most lesbian thing ever, I don’t know what is.
Okay, so finding a lesbian to bang in the Midwest was going to be tricky. Fine. I started to wonder if I could fuck a couple.
But here’s the thing about couples looking for a third in the Midwest. It’s a lot of people who live in the 'burbs and are thinking of it solely as a way to spice up their boring Midwestern marriages (because they don’t know of any other ways to do it). None of them have any experience, and I am no one’s first time and I am no one’s experiment. Ever.
I’m not having my pussy eaten by someone who’s never done it before, Susan. I’m not your present to your boyfriend, Brenda. I’m not schlepping out to the suburbs, Janet. I love myself more than that.
I said to one woman recently hey, if you want to have one-on-one time with me beforehand so you know what’s up, I’m down. Then we can invite your boyfriend to the party. She was SO enthusiastic--excited even--because she had always wanted to do that. But her boyfriend wasn’t cool with it. First, he threw a hissy over the fact that he couldn’t watch (that ruins the experience, BRAD, because then your girlfriend feels the need to be performative and isn’t going to be present and actually enjoy herself, trust me). Then, he admitted that he didn’t want her to play on her own under any circumstances. I understand that, but I also don’t at the same time. I would hope any partner of mine would know that sleeping with a woman (in this context) doesn’t mean anything, be supportive of my sexuality and desire to play alone, and not hold me back from an experience I really wanted.
I was cockblocked by an insecure dude. And that’s fine—because I don’t want to sleep with an insecure dude under any circumstances. Bullet dodged.
When there are experienced couples, it’s great, but it’s very hard for me to find myself attracted to both parties. There’s a lot of this going on:
And OF COURSE on the fourth day of Mercury in retrograde, I accidentally swiped left on two hot dudes looking for a third (I love MFM) on OKCupid. Goddammit.
Women weren’t working out and couples weren’t working out. And then it hit me: you know who isn’t typically looking for a relationship? Dudes much younger than myself. Cut to me going on a date with a twenty-four-year-old.
[The last time my friends gave me the amount of shit I got for doing this was when I fucked a dude named one of the worst names on the planet. Think "Gilbert," but a thousand times worse.]
But there were five great things about this 24yo:
It’s incredible how clear my mind becomes once I’ve had sex. It’s like a tranquilizer dart.
Anyway, the next day, I went on a date with someone I talked to so much via text, I was like fuck it, let’s just have a phone call instead. And then we were on the phone for an hour. A fellow comedy writer, we met for tacos and laughed and swapped stories for a few hours. Then I introduced him to Insomnia Cookies (based in NY! I didn’t know there was one here!) as I groaned while consuming that Stan’s donut. At the end of the date, we both agreed that we didn’t feel a sexual connection, but enjoyed each other’s company a lot (at least I did) and decided to hang out again as friends.
I started getting more dates once I understood that the men and women here are looking for more of a serious thing. It didn’t make me mask who I am as a person (I’d never change myself for the “benefit” of someone else), but it did influence the way I communicated and how much I shared about myself. Then things started to get easier. Plus, the married, nonmonogamous, experienced women started coming out of the woodwork (it just took ‘em a while!), and that was extremely helpful as well.
So far, I love Chicago. The dating scene has been great, the food is incredible, and, honestly, as a New Yorker, it just feels like home. I’m excited what the next month will bring.
I figured this would be a good opportunity to finally talk about Hawaii.
At the end of April, I went to Hawaii on a whim with someone I had met on Tinder and, by the time we left on the trip, had known for 4 months. When he invited me, I had only known him for 8 weeks. As you can probably tell, this story is going to be really short and super boring. I’m sorry, you guys.
When I told my friends that I had agreed to go on this trip, most of my them (understandably) thought I had lost my mind. Many of them feared for my safety—fear that, at the time, seemed silly, but now, looking back, I realize was completely valid. If a friend told me she was going on a two-week vacation to a tropical island with someone she had known for 8 weeks, I’d… well, I’d tell her to go for it. I’m probably not the best person to listen to in this kind of scenario.
I do random shit like this all the time. I have:
Do you understand my vibe now?
When I met Bryan, I was living in Asheville. We matched on Tinder while I had the bio “Pros: Loves anal. Cons: Also loves Chipotle.” He opened with a joke about us getting Indian food. Soon afterwards, I gave him my phone number.
During our initial text conversation, Bryan asked me a lot of questions. Even though I was a snippy bitch to him (a few days earlier, I had gone on a date with someone who didn’t respect my lack of consent—thankfully no physical harm was done to me—and was still rattled), I really enjoyed answering his thoughtful questions because so many men don’t ask me anything. That seems absurd, but I can’t tell you how many dating interactions I’ve had where men haven’t asked me a single question.
After a while, I figured it was my turn. I have no idea why this was the first question out of my mouth—and it’s a question I’ve never asked another person before either—but I opened with: “What is the craziest thing you’ve done recently?”
Bryan’s answer was: “I just moved into a warehouse.”
My response was: “What the fuck did you just say”
As a debatably homeless man, that’s how Bryan’s nickname was born. I started calling him HB, which stands for Homeless Bryan. I asked him for a picture of his “bedroom,” and after receiving it, said, “I’m sorry, but I can’t do this. I can’t get fucked on that table saw. Take care.” His response to my rejection was so kind, he was SO CUTE, and one of my friends was like, “Yeah right, Dana. You can get fucked on that table saw and you know it,” so I caved. After our first date, which concluded when the restaurant had turned its music off and was packing up chairs, we spent the next two days together.
I spent most of those two days giving him shit about living in a WAREHOUSE WITH NO HEAT IN ANOTHER STATE (he didn’t even live in Asheville!). After we parted ways, even though I had given him my usual spiel as I say goodbye to a hookup (which is “if I hear from you again, cool, if I never hear from you again, also cool”), he texted me something disgustingly nice. We kept in touch.
One day, I was walking home from Biscuit Head in Asheville and stopped dead in my tracks. I realized I didn’t have a permanent address and wouldn’t for the rest of the year… which meant I was debatably homeless, too. I texted him this and he laughed.
One thing you need to know about HB is that he’s a total mess of a human. He’s a walking tornado, if that tornado loved nerd shit and the most boring podcasts on the planet. Bryan does the most inexplicably dumb things like buy all 4 versions of Breyer’s vanilla ice cream (Creamy Vanilla, Homestyle Vanilla, Homemade Vanilla, Natural Vanilla—see? I hate that I fucking know this now) and conduct a taste test by himself for no reason, take a 5-hour ADHD test just because he “loves testing and shit,” and invest in bitcoin. He is so dumb, in fact, he invited me on an 11-day trip to Hawaii with approximately ZERO game plan that we had to arrange over the course of less than 2 months. One day in February, completely out of nowhere (no context, nothing), I got this text:
And I’m the stupid, impulsive, unstable weirdo who said yes. Well, my actual initial response to that text was, “Ok but only if you promise me I’ll get lei’d.”
Based on the previous list of stuff I’ve done, while most of my friends were horrified that I was going on this trip with someone I barely knew, my mother just looked at me, sighed, and said, “Of course you are.”
Before we started planning, we set some ground rules:
While we had nearly identical travel philosophies, I also wasn’t stupid. I said I wasn’t buying my plane ticket until he bought his. A few days after the invite, also out of nowhere, I received a screenshot of Bryan’s plane ticket. Well, it wasn’t a screenshot—it was a picture of his laptop with the ticket confirmation pulled up on it that he had taken with his phone. (Did I mention that Bryan’s a dad?) Approximately twelve seconds later, I bought my ticket and sent him an actual screenshot of it like the millennial that I am.
After exchanging travel confirmations, we realized we were on the same flight from Seattle to Kona.
“Make sure our seats are next to each other!” HB texted me.
“Ugh. I have to sit next to you for 6 hours?” I texted back. “No shit I’m going to make sure we’re seated next to each other, I just signed up for 11 days with your dumb ass.”
The tickets were booked. We were officially going to Hawaii, even if at this point we had no idea where the fuck we were going to stay and had seven weeks to figure it out.
The planning ended up being surprisingly easy—all the places we wanted to stay miraculously had availability during the days we wanted. In the end, we decided upon 4 days at an oceanfront house in Pahoa (east side of the island where there are very, very few tourists), 5 days at a farmhouse in Kona (west side of the island), and our final night would be at The Four Seasons just as I had demanded. :)
About a month after we finalized accommodations, I flew from Austin (where I was living at the time) to Seattle, where we’d meet to catch our flight to Kona. We took a selfie and I sent it to the friends who said HB was planning on murdering me and dumping my body into a volcano.
The flight passed by quickly as HB and I shot the shit for hours like we always do. By the time we landed (around 9pm local time), poor HB had been up for nearly 24 hours (because he had flown from the East Coast while I had stayed in Seattle for a few days beforehand and wasn’t jetlagged at all). There was no way his punch-drunk ass was driving to Pahoa. When we picked up the rental car, I had the following conversation with the Avis representative:
Avis: “Are you his wife?”
Avis: “There’s an extra charge of $30 a day for you to drive the vehicle then.”
Me: “Oh hey, guess what? Funny story—we’re married now.”
Avis: "Here are your keys."
And so I drove the 2 hours across the entire island in the dark… in the rain… while stuck behind some IDIOT who was driving ten miles under the 30mph speed limit and BRAKING as we went up a giant hill. HB and I were so tired and dead, we absolutely lost it laughing. We got to our house in Pahoa and collapsed.
When we woke up the next morning, we finally saw our house in the daylight and were dumbstruck. It had two balconies—one downstairs (outside of our bedroom) and one upstairs (outside of the living room/kitchen)—and a pool that all overlooked the ocean. From the balcony, we could see Kehena Beach on the left and one other house in the distance perched on the side of a cliff on the right. That’s it. The rest of it was sapphire blue ocean, palm trees, and rocky shore. It was incredible.
Here is a video because I still can’t get over this house:
For four days, we did as we promised and were complete slugs. We either swam in the pool, went to the naked beach (which was a 5-minute walk away), or relaxed at our house with the incredible views. One night, HB cooked us dinner and discovered he has a pineapple allergy (“My tongue hurts!” - the last thing HB says before he dies) and another night we went to the weekly open-air night market at Uncle Robert’s Awa Bar where we were 2 of the few tourists in a sea of a hundred locals. It's impossible to capture the breadth of the entire market, so here is a small snapshot:
One of my favorite memories will always be lying down on the shore of Kehena Beach, completely naked, and feeling the sun on my face as the waves licked my feet and rolled up to my waist.
Living in Pahoa was one of the most relaxing experiences of my life. There was no schedule. There were no obligations. I was off my phone 90% of the day. The only time I was on my phone was when Bryan and I got horrible idea to troll my friends. And by horrible I mean downright amazing.
Bryan and I decided to get engaged. Five times.
I don’t remember exactly whose idea it was, but I wear a diamond ring on my middle finger that was a gift from my grandmother and, you guessed it, it looks like an engagement ring (though it’s not—Hilda just has mad game). The first time we got engaged, Bryan and I flagged down an older man and his elderly mother (on her birthday!) driving by and asked them to take some photos of us on some lava formations. Then I posted the pictures with the caption “Still in shock. This man is always full of surprises. #engaged”
And then I waited. It wasn’t long before the flood of texts started to come in. I wasn’t sure what to do.
“It’ll be more believable if you go dark,” HB, a literal demon, suggested. He was right. As someone who usually texts back in a timely manner, when I didn’t respond, my friends started to panic. (These texts below are all from friends; I found out later none of my actual family members texted me because they had been sending my mom congratulatory messages, LOLOL.)
I thought that with each subsequent proposal, if I tagged each post on Instagram with the exact same caption every time, surely my friends would catch on. They did not. [“We all believed it because your dramatic ass WOULD make someone propose to you multiple times,” a friend told me afterward. I have never been more offended.]
I don’t know what it says about me that people who’ve known me my entire life would think I would get engaged to a man I had known for 4 months. I don’t want to think about it.
After 4 days of living in absolute paradise, we drove our car across Big Island to our farmhouse in Kona. The house was located on a coffee farm and beyond the rolling hills of tall leafy plants, you could see the ocean. It also had orange trees lining one side of the house and we were told we could pick them and juice them (though we never did because we started each morning with a nice, healthy mudslide). Despite chickens roaming the property and an outdoor shower, the house itself was very chicly decorated and featured a huge kitchen, gigantic bedroom, and tall ceilings. It was beautiful.
“Oh darling, it’s so nice to be back at the country home after four days at the beach house,” HB and I teased each other as we pretended to be wealthy socialites.
The next 5 days went something like this:
The silliness and laughter looked a little something like this:
While we were in Kona, we were no longer slugs. We traveled all over the place. HB wanted to visit some coffee farms and even though I was a less-than-enthused brat, I’m glad he convinced me to go because they were really pretty and fun to walk through.
Here are the beaches we checked out:
1. Hapuna: What I think of when I think of a “typical Hawaiian beach.” Water was super calm and beach was very accessible (some of these beaches require you to walk on some rocky parts for a bit). It's very family-friendly. I don’t have any pictures of the beach by itself because it was a cloudy day, so here is a picture of me beating the shit outta HB:
2. Waialea: Absolutely gorgeous. There are a bunch of fallen and low-hanging trees on the shore, so you can set up camp and essentially make a little carved out, hidden cove for yourself. The water was completely still in some parts and rough in others. I went out and floated in the still parts and never wanted to leave.
3. Kua Bay: This place was insane. It is PERFECT for bodysurfing. The waves were huge, but if you swam out far enough, they wouldn’t crash on you and you could catch a ride on the giant swells. HB even saw a sea turtle swim by us! We also stayed late and watched the sun set and when I sent pictures of it to my brother he texted me, “Are you sending iPhone wallpapers? What the fuck.”
4. Kealakekua Bay: This is the famous snorkeling beach. We admired the candy-colored fish and lace-like coral formations before running into some unexpected visitors.
Though I seem relaxed in this video above, I had experienced a panic attack. There is absolutely nothing creepier than having your head submerged while swimming out into deep waters and hearing the chirps of wild dolphins you can’t see. When we started getting close and I saw a dorsal fin flash by HB’s head, I had visions of his arm being ripped off by dolphin teeth like some Final Destination shit. I stopped and treaded in place, pushed my goggles to my forehead, and told him between gasps—my voice 14 octaves higher than normal—I couldn’t do this. HB swam back over and said we didn’t have to do it if I didn’t want to.
But I didn’t want to be held back by fear. Though I was close to hyperventilating and my stomach was in knots, I was angry at myself for being scared and holding back my own damn self (and HB) from an experience. I said out loud to myself, “No, I’m fucking doing this.” Then HB grabbed my hand and we swam over together.
During the first few moments of our nose-to-nose (or I guess I should say nose-to-snout) encounter, I squeezed HB’s hand so hard I felt like I was going to snap off his fingers. But once the first dolphin glided by us and I watched it cut through the salty ocean with silent grace, it sunk in. We were actually swimming with dolphins out in the wild. So close that I could almost reach out and touch these creatures. It was absolutely indescribable. Beautiful, really.
I had never done one of those fabricated “swim with the dolphins”-type experiences before solely on principle and I’m glad didn’t. Swimming with wild dolphins, while somewhat dangerous, is... there are no words. To say it's incredible doesn't do it justice. We swam with a pod of about 40 dolphins for close to two hours and when we returned to shore, they had disappeared.
We had some other adventures, too.
When driving into Kona, we saw this sign, immediately looked at each other, and cackled. “Why would somebody brag about that?” HB asked.
But it turned out to be really good! HB even asked the cashier how they made their fries. I guess what I’m trying to say is that everyone should try the 8th best cheeseburger in the US.
We tried some local favorites like Kona Brewing Company (the only thing I remembered us eating was the roasted garlic appetizer, which is the appetizer of my dreams), Broke da Mouf (get the pork! and the purple potatoes that I LOVED and HB hated), and Umeke’s (I don’t eat poke, but the short ribs were incredible).
We also had another interesting dining experience… completely by accident.
Before I left for the trip, I had asked one of my coworkers who had grown up in Hawaii for some restaurant recommendations and one of the places he suggested was Kamuela Provision Company. The place had a fancy menu, it overlooked the ocean, and I was feeling bougie so I asked HB if we could go. We typed the address into the GPS and as we drove up to the place, I felt a dark cloud settle over us. The restaurant was located inside… a Hilton Resort.
HB and I had found ourselves in Wristband Country.
As we walked through the Hilton, we passed middle-aged Midwestern tourists with their khakis and socks/sandals combos. These were fine, upstanding people who came to Hawaii to never leave the resort (that’s not a real travel experience! it’s the reality television version!), not traveling heathens like me and HB. I grabbed HB by the forearm and urgently whispered, “We can’t be here.”
One of the reasons we couldn’t stay was because HB and I love to engage in a rather… for a lack of a better word… unique pastime. We love to fake argue in public. To the point that it becomes a screaming match and we attract stares. I have no idea why it’s so fun.
Some things HB and I have argued about are: whether salsa has any nutritional value, why I wouldn’t miss bananas if they ceased to exist (HB was HORRIFIED by this), if dolphins killed people on a regular basis, why bodysuits are called bodysuits and not catsuits (I DIDN’T NAME THESE GARMENTS, HB), if hotels research their customers before they arrive to see if they need to give them any special treatment, how emotionally unintelligent HB is and why I consider him to be an emotional terrorist, etc etc.
I knew we would get kicked out if we fake argued at this restaurant, so we turned around and hightailed it out of there. I think my sandals were on Hilton property for all of 4 minutes.
When we left the gates of the Hilton, I almost wilted with relief. As we started driving toward our Airbnb, HB asked me to go on Yelp and find us a new place to eat.
And that’s where I discovered Privateer’s Cove.
Here are some actual excerpts from reviews of Privateer’s Cove on Yelp:
“What he wants to do is sing a very bawdy, profane sea chanty. Maybe this is an authentic pirate song? I dunno. But it isn't funny, it is just dirty, liberally featuring the c-word. We aren't entertained, and yes we are slightly offended.”
“You’ll either love it or hate it here.”
“Probably not for everyone.”
I turned to HB. “We’re fucking going here.”
There are a few things you need to know about Privateer’s Cove: first, it is a pirate-themed restaurant next to a laundromat inside a strip mall. The whole restaurant’s schtick is that the waitstaff is rude to you. The food is perfectly prepared and fucking delicious (I had a steak and HB and I shared a creme brulee). While there’s a fully stocked bar behind the counter (“That’s for the staff” – the cook), if you want booze, you have to purchase it from what I can’t imagine is a legal alcohol brewing storefront connected to the restaurant. HB left to get us something and returned with a mason jar of “passionfruit”-flavored vodka (trust me, putting passionfruit in quotes is GENEROUS) after being forced to taste test a bunch of hooch.
“Why on earth did you get this one?” I asked HB after I took a sip and it burned off the top three layers of cells in my esophagus.
“Because it was the most disgusting one and I wanted to fuck with you,” HB replied cheerily.
While the older couple at our communal table was scared shitless, being the vagabond weirdos we are, Bryan and I fit right in at Privateer’s Cove. The waitstaff’s gag may have been to give us shit, but I’m a tough New York bitch and so I gave it right back. We definitely had some old timey guns and swords pulled on us as a result. After all the patrons left and the restaurant was technically closed, HB and I were invited to stick around and sing sea shanties.
You heard me right. Sea shanties. For three hours. Call me romantic, but this one was my favorite:
The best thing about Privateer’s Cove is that they had a printed book of about 100+ sea shanties that Bryan and I had assumed were known pirate hymns. That would make sense, right? Nope. They were all written by the owner. And the staff knows the words to every single one of them.
I don't remember how much I drank that night, but let's just say that I smoked a bummed cigarette for the first time in about 8 years and leave it at that. The whole night, between shouting profanities, HB kept leaning over and whispering, “Hilton. We almost ate at the Hilton.” I was laughing so hard, I was in tears.
The next day, we went from drinking nail polish remover next to a laundromat to checking into The Four Seasons.
The Four Seasons is an excellent place to stay if you are sophisticated, rich, and classy.
I am none of those things, so I decided to troll them, too.
By that time, Bryan had proposed to me four times and had decided it was now my turn. While he may have had me beat on quantity, I was determined to beat him on quality.
One night while we were at our country house, HB, the dumbest man alive, complained that he had a hankering for Chicago deep-dish style pizza and actually called restaurants on the island to see if any of them served it. Earlier in the day, we had been trying to think of a plan of how I would propose to him at The Four Seasons. This was before I had told HB that the only place you can find that kind of pizza was in Chicago.
I was right. The place you could get that kind of pizza was Chicago. And so I overnighted two pizzas from Chicago and asked the most expensive beachside restaurant at The Four Seasons to cook it for us because I was proposing to my “boyfriend.” I may or may not have spent $250 to do this.
They fell for it.
So much so that upon checking in they kindly informed us that we had been given a $600 room upgrade.
That night, I proposed to HB and it was fabulous.
We couldn’t have spent our last night in Hawaii in a better way.
The next morning, I cried… because I didn’t know when I was going to see my friend again.
You spend that much time with a hilarious monster and tell me you’re not going to miss him. G’head.
I actually wrote down a list of the funniest things HB said to me because I didn’t want to forget them:
“I’ve eaten a rotisserie chicken over the sink, happy as a clam.”
“My charm and my looks get me out of so much trouble. Like, if I didn’t have a nose, I’d be in jail.”
“I’m pretty normal.” (This one I scream-laughed at before screeching YOU WERE HOMELESS AND INVITED ME ON A HONEYMOON AFTER KNOWING ME FOR 8 WEEKS)
After HB left (his flight home was before mine), I spent the rest of my time in Hawaii alone. I drank smoothies from my private cabana. I got a spa treatment that included a coconut oil massage, a coconut scrub, and being wrapped in what felt like a warm flour tortilla. I swam in the pristine Four Seasons slice of beach and breathed in some deep breaths of gratitude. I realized what a difference a year makes. Twelve months prior, I had gone through one of the hardest periods of my life. I relied on my network heavily as I tried to navigate absolutely everything around me falling apart. (In fact, me having nowhere to live sparked the creation of this trip.) Now I was at the fucking Four Seasons. I had just spent 11 days in paradise laughing to the point of physical pain. During my remaining 6 hours in Hawaii, I didn’t cry. I was beaming.
When I returned to Austin, I took off all my jewelry to put on my bed stand for the night and noticed there was a grain of black sand from Kehena Beach stuck inside my engagement ring. I tried to dig it out, but it wouldn’t budge. After a few minutes, I stopped trying. I figured carrying around a piece of Hawaii with me wasn’t a bad thing.
I know, I know. I post to “Eat, Drive, Fuck” faithfully every week, but that didn’t happen last week. But I have a good reason, I promise.
The first—and biggest—reason I didn’t publish anything last week was that I wrote an AMAZING post that is the longest I’ve ever written for this blog, FULL of pictures and videos that I'm really, really proud of (and it took a lot of time!)… and then had to delay posting it for very exciting reasons. Stay tuned. [There is a separate, HUGE announcement at the very end of this post!]
Next, I drove from Denver to the Grand Canyon (which was just as fabulous as I’d hoped it would be) to Phoenix to LA all in the span of a week.
Then I left my car in LA and caught a red-eye to New York. I had to come home for a specific event for my day job and my father’s surprise 60th birthday party and so I tacked on an extra few weeks to see friends, have a meeting with my agent, and talk to some lovely people I met at the sex therapy and education conference in Denver.
Essentially, I had 21 days to fit in meetings with 347 people. It’s been so fun, but also exhausting. I also think I have a bit of an emotional hangover because this past Friday, I visited my old neighborhood in Queens—my home before starting this trip. It was more emotional than I thought it would be because I thought of how far I’d come (both figuratively and literally since I had lived in NY my entire life) since I left.
As I walked around Astoria, I passed the shitty diner where I’d get bacon, egg, and cheese sandwiches after late nights at hookups’ apartments, the laundromat where I was SO EXCITED when I finally started making enough money to drop off my laundry instead of doing it myself (dropping it off cost $30/month, btw), and the super cheap massage place I frequented every few months that still gives off major hand job vibes. To get to my old apartment, I took the train I passed out on multiple times on my morning commute due to stress and exhaustion caused by my job in book publishing I left two years ago (that job also caused me and other coworkers to miss our periods!).
My first job out of college (in my industry) paid $27,500 a year. If that sounds like not enough money to live on in the city, you’re right. It isn’t. I spent 4 years living at home, commuting 4 hours every day to Manhattan and saving money. By the time I moved to Queens in 2014, I had paid off 60% of my $100k student loan debt and written 4 books for HarperCollins (under a pseudonym because it's a genre I don't even read) solely for the money. By then, I was making $38,500 a year, which is still not very much considering NYC is the second most expensive city in the world. I very much remember the years of having to walk 22 blocks every morning to save the (at the time) $2.25 subway fare, considering a weekly $5 cup of soup for lunch a “treat,” and stealing rolls of toilet paper from bathroom stalls at work because it meant one less expense.
I also remember the shitty people I dated and the shitty sex. Oh how I remember the shitty sex.
I’ve dated Russian bankers who claimed that me using toys “threatened their masculinity,” insufferable photographers who had more opinions on obscure music than an actual sense of self, freelance film dudes (For the love of god, save yourself. Never date these men; they are man-children) who were about as exciting in bed as a Wes Anderson movie.
I fucked office temps, sommeliers, a literal sex addict who worked in international aid, advertising executives, a guy who worked at an Apple store, a producer at a very well-known television show that’s still on the air, a special ed kindergarten teacher (I mean, come on, just bend me over already), Broadway dancers, and a very memorable voice-over actor in Williamsburg who ate my pussy for 4 hours straight on my 28th birthday. Him and the kindergarten teacher were great in bed. Everyone else? [farting noise]
And during the three years I spent in Astoria, while I fucked a lot of lackluster men, I was busy building a career. I was editing 900 pages a week at a thankless job that gave me zero weekends off and kept telling me I was not good enough (despite the books I worked on selling really, really well) so they had an excuse not to promote me (the company was hemorrhaging money). I was taking the N/W train every day, which is a job in and of itself. I have no idea how I did it, but I carved out small slivers of time to write for magazines on the side. My then boss made it very clear that she was not supportive of this, but I didn’t want to stop. Between being broke, dating stupid people, and suffering at a job that was working me to death, sex writing was the only thing that made me happy.
I used to see a therapist near Central Park South once a week on my lunch break, my only reprieve from my hellish job. During our first session, she asked if I could not eat the salad I had brought because it was distracting.
I looked at her, dead-eyed, and said, “I have to fucking eat.”
“Well,” she replied, “At least I know you’re assertive.”
No joke, that therapist went on to get murdered by someone, which was a shame because she was a really good therapist. Ah, New York City.
With a dead therapist and an unsupportive, micromanaging boss who apparently didn’t want me to have a life outside of work (which is very often the case in book publishing, unfortunately), I decided I had to leave. I was scared shitless to make a drastic career change, but I wanted to write and I wanted to get my fucking period again. I found a generic front desk job at a tech startup that paid more than what I was earning as an editor making a name for herself in the industry (outside of my boss, people actually liked me and my work a lot) where I'd write more. At the time, I had purple/green/blue/pink hair and took my mom out to lunch in the East Village to break the news to her. I was ashamed that I was leaving the industry I had specifically gone to NYU for. As someone with an incredibly blue collar, middle-class upbringing (both my parents didn't go to college), I grew up to value stability. I was taking a huge risk by trying out this whole freelancing thing.
"I don't want you to be embarrassed that your daughter left a career as an editor to become a receptionist," I told her at some outdoor cafe near Tompkins Square Park. "What will you tell our family when they ask about me?"
"I'll tell them what I've always told them when they ask about you: that you're a writer," she said.
I saved a photo from that day.
At my new job, I dyed my hair black (I had dyed it blonde for the interviewing process, but, as much as I loved it, bleach made my hair fall out and I didn't want to look like Cynthia from "Rugrats") and wore jeans and combat boots out of necessity. Between buzzing people in, stocking the kitchen, and literally shop vacuuming overflowing toilets, I sat at my desk and wrote. A month later, my first story got picked up by Cosmo. Six months later, I became a contracted contributor to Playboy.
At this time, I started dating the person who I thought I was going to marry and he lived very far away. Every Friday night, I commuted 3 hours upstate (one-way) to spend the weekend with him. On Monday mornings, we’d wake up a little after 5 so I could be in Union Square by 9. I did this for a year. Actually, what I should say is: I have no idea how I did this for a year. The constant back and forth was incredibly draining.
About 6 months into my new job at the tech company, I got approached by the then VP of marketing. Because I sat at the front desk, I knew all of my coworkers by name and was friendly with almost everyone. One day, this VP came over to ask a question about our company’s commuting benefits or something and he happened to ask where I worked before I came onboard, thinking I had been a front desk person somewhere else. When I informed him that I had ten years of experience as an editor, he asked why the hell I wasn’t working on his team. Soon, I started editing marketing materials. By the time things were getting serious with my partner upstate and I had plans to move, through a series of circumstances, I was given a full-time remote position in marketing. Between the new remote gig and discussions of engagement rings, I got rid of my apartment with the intention of moving upstate.
And then the breakup happened. With nowhere to live, the idea for this trip was born. Since I left Astoria last June, I’ve lived in Boston, Asheville, Austin, and Denver, I’ve driven across the country on my own, I went on the best (and most impulsive) vacation ever to Hawaii, I got published by 4 new publications (including my dream one, New York Magazine), I got published in print for the third time, I’ve been interviewed by Buzzfeed and (soon) national television, I’ve fucked some truly gorgeous (inside and out) people, and I've figured out a lot of things for myself. I’ve been hustling, y’all. And I’ll continue to hustle.
I went from making minimum wage and editing other people’s work to having financial stability for the first time in my life and traveling across the entire country while writing things I'm passionate about. I recognize I had a ton of privilege while moving up this ladder, but a lot of blood, sweat, and tears went into it, too.
Between my jam-packed schedule while I’m back in NYC and looking back at all the work I’ve done over the last ten years, I decided I need a tiny break.
Next weekend, I move to Chicago for the last “big” leg of the trip (6 weeks!). After Chicago, I fly to LA to pick up my car and drive up the PCH to Portland, where I’ll stay for 3 weeks before driving back to the East Coast. The gift I’ve decided to give to myself right now is self-care. In Chicago, I plan on being on my phone less, reading actual books more, learning how to box, cooking more (and I don’t mean just heating up veggie burgers and eating potato chips, DANA), going to the beach, and writing some chapters of a new book. I also plan to masturbate more.
Because here is the big announcement (one of a few more to come over the next couple weeks): I’m going to start doing sex toy reviews on my website.
This decision happened after learning that toys—just like so many other products featured in magazines—are given false praise by online publications in exchange for a cut of sales. As someone who believes in only providing 100% truthful information about sex, masturbation, and sexual health, I consider this practice to be Grade A horseshit. So I’m going to start writing some myself.
Not even a day after coming to this conclusion via a conversation with a PR person I know and love (who is just as horrified by this practice as I am), I was asked if I wanted to become a brand ambassador for a company called MedAmour, a startup whose focus is making the act of buying sex toys less scary, ensuring quality control, and helping those with medical conditions that can make sex uncomfortable or downright impossible (including vaginismus, endometriosis, etc). Its stock is carefully curated so that new customers aren’t overwhelmed or intimidated, and products are appropriate for those just beginning to broaden their sexual horizons. You will not find any scary-looking, intimidating, or "advanced" toys on this site. The owner had the idea for this company when she realized sex therapists were recommending certain toys to their patients, but weren’t recommending specific brands or where to go. And that led to three big problems: confused people not knowing what exactly to buy, finding cheap toys on Amazon (Where the quality isn’t controlled! Never buy sex toys from Amazon—many of them aren’t body-safe!), and/or going to large brick-and-mortar stores and being so overwhelmed that toys never got purchased.
I’ve been asked to partner with some companies in the past and they were either things I was not particularly interested in (if I get offered a partnership with a tampon company one more goddamn time), didn’t seem beneficial to people who follow me, or the company owners had a less than stellar reputation. I truly believe in MedAmour’s mission and I want to support a woman-owned-and-operated business. If I can write honest toy reviews and then be able to offer discounts to people who want to buy the toys I recommend, then that is a win for everyone. I'm not doing this for the money (and the money is very small, trust me), I will only recommend toys I absolutely love, and I was going to write the reviews anyway, with or without this partnership. I want to destigmatize toys (after all, they are a HUGE part of creating an amazing sex life--check out tip #3!), provide people with accurate information about them, and support a business whose mission I fully believe in.
And to prove that I’m not being a shitty “influencer” dipshit who’s peddling crap that sucks, my first giveaway with MedAmour is going to be… A WOMANIZER STARLET (worth $89!). If you’ve followed me for a while, you know that I have talked about this toy for years and consider it a must in any vulva-haver's collection because, get this, it’s a CLIT SUCKER. Here’s me raving about it in September of last year, where I say, “It’s almost indistinguishable from real oral sex, you can orgasm in under 3 minutes, and you don’t have to listen to a cis male talk about The Smiths afterwards.”
It’s also the toy that consistently makes me squirt when combined with penetrative sex. On this trip, I’ve squirted while using it with two different former-Bible-thumpers-turned-agnostic-nonmonogamous-people! It is truly the Lord’s toy.
I look forward to bringing you my signature blend of candid, informative, and, at times, humorous real talk about a bunch of sex-related products. I can’t wait to talk about my love of dilator sets (I used one as a teenager!), anal play, and the newest clitoral and penetrative toys on the market. It's gonna be so much fun and I hope you feel empowered to try something new!
I made it to Arizona, the first place where I’ve had to make sure I brought all of my luggage inside so that my dildos wouldn’t melt in my car. The heat here is an EXPERIENCE.
The rest of my time in Denver was great. My sex friend and I exchanged gifts before I left. He made me 4 mixed CDs (my car has a CD player, lol), including one he titled “DanaMash,” which starts with the song “Sex Machine” and includes at least 6 songs about big booties. In return, I made him this:
You're damn right I framed it.
You’re just going to have to trust me on this one, y’all, but please know that I only give praise when it is deserved (more on that below!). I shall miss that dick (and the dude it is attached to).
But yes, I drove to Arizona so that I could stop at the Grand Canyon. I did the classic thing where I thought about my life and how small I am in the universe. Many people have existential crises at the Grand Canyon and, to be honest, it’s kind of hard not to. I thought about my place in the world and what I want from my life. And that made me think about the conversations I’ve been having lately about autonomy, bravery, and creating a joyful life—and a big part of that is creating a joyful sex life.
I recently had a friend tell me she wanted to delete Tinder because, over the last 6 months, had only met “one cool guy and two cool girls.” I laughed really hard at that. Then I told her I had been on multiple apps since last October and had met three cool men in Boston, one in Asheville, and one in Denver. I think there’s a perception that dating just comes really easily to me and the hot men I fuck cross paths with me solely because of luck. There’s also a perception that at the beginning of this trip (eight months ago), I just flipped a switch and gained a really amazing, exciting sex life. Or that I've always had one because I am a sex writer.
Holy shit NO. No, no, no.
It’s so not that. Creating this life took a lot of hard work, a lot of failure, a lot of gaining life experience and learning from mistakes, and a lot of sticking to my guns even when it was really, really hard. Up until four-ish years ago, I was having pretty crappy sex—the kind of sex people would describe as “average” and come to know as all that sex could be.
I no longer have crappy sex. And I want other people to no longer have crappy sex. Thinking of people accepting the kind of sex I tolerated for so long actually makes my heart hurt.
When it comes to how and why I have a great sex life, I really thought about it. And then I pulled together these ten reasons why my sex life is the way it is:
1. I don’t follow the sexual script. When I went to the conference for sex therapists and educators last month, the idea of a sexual script was explained to me by Dr. Laurie Mintz. It’s something we all kind of know, but I’d never heard it articulated before. The sexual script goes like this (for couples where one person has a penis and the other has a vulva): kissing, light touching of breasts or vulva, oral, penetration, orgasm by person who has penis. The end.
This script, I’ll admit, is something I followed for years. Then I thought… why does sex have to look like that every time? Why am I following a “formula” that doesn’t value me as an equal partner (i.e. I’m not guaranteed an orgasm in order for the sexual encounter to be considered complete)? Then I did the best thing I ever did for myself: I abandoned it.
The way I think of sex now is: let’s write down on a whiteboard all the things that are sexual or sensual. Sure, it would include all the things I’ve mentioned in the sexual script, but it would include some other things, too: things like manual stimulation (fingering), anal, massage, cuddling, spanking, playing with toys, mutual masturbation—and so much more. What if you and your partner looked at this board and decided together what you wanted to do? “That looks fun,” “And so does this!” etc. etc. Sex could be performing oral on each other and that’s it. Sex could be a massage and then some anal. Sex could be a spanking session and then getting fingered. Sex could be every single thing on that list! At the end of the day: what would sex look like if there were no rules? Throwing away the script has vastly improved my sex life.
Also, there is a hierarchy in terms of what makes you come and that’s bullshit, too! Apparently, orgasms from P-in-V sex are “better” than those achieved in other ways. But I come the hardest from being fingered! Does that make me “broken”? No! Are orgasms from some things more intense and feel better than others? Yeah! Is it different for everybody? YES. Let’s stop thinking that any method of achieving orgasm outside of penis-in-vagina sex is inferior. [One of my funniest memories: I once had an ex who said he “felt bad” that the last sex we ever had before we broke up was anal. (So if you put your dick in the hole that’s an inch and a half north, it would have been “more meaningful?” LOL he was such an idiot.) I was actually SO happy he said that to me because it made me feel so much better about the fact that he is my ex.]
2. I am incredibly comfortable naked. Now listen. This one took a while. I was once an eating disordered person, so I very much remember what it was like to hate my body and not be comfortable in my skin. And then something happened when I was 24 (when I was already five years recovered from bulimia!) that changed me. I was dating some guy who lived in the Lower East Side and after a sex session, he got up to get something from the kitchen and I walked across his apartment past him to the bathroom to take a shower. (Ah, the days of Young Dana, where she used to sleep over—I was so sweet back then. Now I’m that cartoon sound effect that’s like zoooooom and then there’s a cloud of dust.) It was such a simple thing, but in the moment, I was terrified. Then thought to myself: why am I scared? Why on earth would the person who just had sex with me be turned off by me walking around his apartment naked? He… just had sex with me. He’d already seen me naked. So why did I care now?
And that’s the thing: if someone has had sex with you, they’re already into what you’re workin’ with, so why be self-conscious? (And if they’re not—if they make any sort of negative remarks about your body, make sure to wish them good luck with their rib removal surgery that will enable them to suck their own dick while you're on your way out the door.) Plus, something I always think of is how I’ve noticed “flaws” (I put this in quotes because I don’t believe in any physical attributes being flaws—but I do recognize there are things considered as such by society) on my partners: birth marks, hair growing in weird places, low-hanging balls (this guy I’m thinking of in particular was also the best pussyeater I’ve ever encountered), whatever. I notice these things about my partner as like a “oh hi there, physical attribute,” but I don’t judge them. And I realized that's how people must think about the things I have felt weird about with my body in the past—sexual partners may notice my weird pinky toes or the fact that my body hair grows like fuckin’ Tim Allen’s beard in "The Santa Clause" or my back tattoo (hey, it was 2007), but they don’t care about them. And half the time, I’m sure they don't even notice that shit in the first place.
Getting comfortable with your body takes a lot of hard work and practice! It’s not an overnight thing! Try sleeping naked for a night or two (this was super helpful to me—and I felt so uncomfortable at first). Walk around your bedroom naked while you do chores. Get stoned and dance around naked (my personal favorite). Also, another way I got comfortable naked around another person was introducing an element of relaxation to it! I’m a big fan of massaging people. If you’re going to grind on a person’s naked body, don’t you want to explore it a little bit first? Don’t you want to learn what feels good to your person? When I engage in a sexual relationship with someone, I always take time to massage them. This may make people feel a little vulnerable and I get that. But I promise you that if your partner can’t make you feel comfortable while giving or receiving a massage, sleeping with them probably isn’t the best idea.
3. I consistently use toys during sex. Repeat after me: sex with toys is not inferior to sex without toys. Say it again. And one more time. Thank you. Because something we need to remove from our society is this notion that for sex between a penis-haver and vulva-haver, a penis and a vaginal canal are the equivalent pleasure centers. They’re not. We should be teaching in sex ed that it’s the penis and the clitoris. And guess what? During penis-in-vagina sex, it’s important to have clitoral stimulation, whether that comes from someone’s hand or a toy.
Some toys I recommend during sex are: the Vesper Crave (it’s a necklace and surprisingly powerful—but quiet—vibrator) because it’s long and thin and is small enough to be used in any position without getting in the way, the Womanizer Starlet during any position where the pubic mound of each partner isn’t pressed against the other (ex: doggy, missionary where the man is maybe on his knees instead of flat on top of his partner, man standing/woman lying down on edge of bed, etc), and a bullet vibe with a remote during any position that involves lying on your stomach (like anal). Before understanding the importance of clitoral stimulation in penetrative sex, it baffled me as to why women would ever enjoy receiving anal or analingus. What was the point? And I was right—there is very little point when it comes to anal play on its own if you are trying to achieve orgasm. BUT WHAT NO ONE TOLD ME IS THAT ANAL PLAY WITH CLITORAL STIMULATION IS INCREDIBLE. A bullet vibe on your clit during anal? Holy cannoli. Amazing. And a toy on your clit while getting your ass eaten? It’s practically heaven. My point is: don’t shame toys. If you subscribe to the idea that only sex without toys is worth having, I can guarantee you that you’ll be having fewer orgasms. Anything that can get vulva-havers to come more during sex is a win in my book.
4. I embrace the things that make me feel sexy. There is nothing more fun to me than buying lingerie. It is my ultimate self-care. And I know this can be scary—like buying a bathing suit. But think of it this way: trying on lingerie is dress up. And it’s not to be seen by just anyone, unlike if you were going to the beach. If you think of it that way, it takes a lot of the pressure off. I buy very fancy silk lingerie from places like Journelle and I buy super inexpensive stuff for, like, $12 from random sex toy stores or online at Yandy.com. It doesn’t matter. I also identify as a sub and truly enjoy doing things that will psych up my Dom. I had someone recently ask if I could wear a cotton thong in a light color so he could see how wet I was. Running out to buy one before I saw him? A huge turn-on and very thrilling. Seems like it was something for him, but it was absolutely for myself. Sending pictures and videos also makes me feel sexy! Never send one solely for the pleasure of someone else (unless you truly get off on it). I’m not one of those people. Exchanging pictures is only fun for me if it’s mutual (AND ONLY WHEN I SOLICIT THEM).
5. I have masturbated. A lot. I would say I masturbate as much as a teenage boy, but that’s bullshit. I masturbate as much as a teenage girl because they’re just as horny; we just don’t talk about it. But yes, I masturbate because the best sex comes from teaching your partner how to get you off. When it comes to achieving orgasm, no style is a one-size-fits-all kinda deal. We all like different things. One of my least favorite things is when a guy tries to finger me the way his last partner liked it. (I have literally grabbed the wrist of a guy fingering me WAY too fast and hard, looked him square in the eye and said, “I’m not going to come like that.”) My clitoris is a snowflake, dude! Let me show you what’s gonna work. And that’s the thing—if I don’t know what I like, how am I supposed to articulate what I need to my partner? Masturbation leads you to be more in tune with your body and better equipped to teach your person how to get the job done. Knowledge is power!
6. I play. I don’t box myself in. I identify as a sub, but BDSM sex is not the only kind of sex I have. Not by a long shot! I like everything—slow and tantric, rough and hard, silly, adventurous, the list goes on and on. I see so many people who find themselves saying, “I like x, so we only do x” and that really limits you. I’m not advocating for abandoning the things you know you like (I’ll never abandon BDSM!), but how will you know what you do and don’t like if you don’t play? My saying is, “Always try everything twice… or else how will you REALLY know if you like anal?”
7. I don’t fake orgasms. Ever. Faking orgasms is a gross disservice to both yourself (because you deserve to come) and your partner (because you’re not teaching them what you need in order to come—and how are they going to learn otherwise?). When you fake an orgasm, it tells signals to the other person that the technique they used makes you come… and then they will continue to do it… and then you will continue to what? Oh right. Not come.
Most vulva-havers feel pressure to fake it when they feel their orgasm is “taking too long.” Here’s what I’m going to say to that: it will take as long as it needs to take. There is no reason to feel guilty. I guarantee you that your partner would rather you have a genuine orgasm if it means servicing you for another ten minutes than you faking it. I promise. And if you’ve ever blown a penis-haver, YOU KNOW that sometimes they take a while, too! We should all be entitled to whatever amount of time we need in order to come. And sometimes that time will be shorter or longer than others. Sex isn’t a science! Porn has taught us that people should come multiple times in, like, ten minutes, but we all know porn isn't realistic. The vast majority of the time the women are faking (even the lesbian porn!) and the men are taking breaks and gettin’ fluffed between takes, y’all.
8. I bring up testing. Absolutely no sexual experience is worth the price of me contracting an STI. Even the absolute best sex of my life. I’ve been asked many times by others how to bring up testing with partners—especially casual ones. “I can’t exactly talk about it with the guy I bring home from a bar,” they tell me. And my retort is always, “But… can’t you though?”
My go-to line is, “Hey, I have a six-month rule. If you haven’t been tested within the last six months, I don’t play with you. No exceptions.” The perception may be that it’s too off-putting, but, in reality, I get a lot of respect for sticking to my guns and for prioritizing my health and my partners’ health. I’ve only had one person be scared off by it (and if someone is scared off by that… do you really want to sleep with them anyway?). Mostly, I get people who promise to get on their shit and then a few weeks later we play! I can’t enjoy sex when my mind is worrying about STI risk. If I know I'm being safe, I can be fully present and happy. I’ve also had friends ask me, “Well how do you know if they’re telling the truth if they say they’ve been tested?” And to that I can only say that I use my best judgment. I can tell when people are lying. (And, honestly, only a sociopath would lie about something like that.) Most of the time, people offer to show the receipts, which is great! And if they don’t offer and I feel the need to ask for them… that means I don’t really trust them and shouldn’t fuck them.
9. I only date people who value my pleasure. Years ago, I had plenty of sexual experiences where I didn’t come and said it was “fine.” (How many times, vulva-havers, has that happened to you? It’s a very common experience.) After all, I had grown up on the cultural messaging that women weren’t meant to come every time, that orgasm is harder to achieve for women than it is for men (wrong), and that sex ended when the penis-haver orgasmed. (Vulva-havers can be brought to orgasm as easily as penis-havers. There are actually studies that support this. If you're a vulva-haver, think about how "difficult" it is for you to orgasm via masturbation. The idea that you can't orgasm as quickly as a penis-haver is a crock of shit, right?) Then, after about four sexual experiences with a guy I never came with, he finally went down on me, got me THIS close to orgasm… and then he gave up. I almost kicked him in the head. Never again, I said to myself. I would never date someone who didn’t care if he got me to orgasm. Over the last 8 months, with the exception of one person, I have only dated givers, which are men who get off on their partner getting off. (And that one person who wasn't a giver got kicked out of my apartment.) My most recent partner (who received the best dick award!) refused to come until after I came at least 3-4 times. After knowing that there are men out there who are like this, I will never settle for anything less. And pleasers are a lot less hard to find than you think they are.
10. I don’t settle or tolerate bad sex. You deserve someone you’re super attracted to. You deserve someone you don’t feel just “meh” about. (Sex also feels better when you’re super turned on! You’re wetter, which makes things more comfortable, and, believe it or not, when you’re more aroused your vaginal canal can expand up to 7 inches to accommodate a big ol’ dick!) You deserve someone who cares about your pleasure. Guess what I do when someone clearly doesn’t care about getting me off? I fucking leave. This attitude took a while to develop, too, because it takes some major balls to get up, put your clothes on, and tell your partner to quite literally fuck themselves. (And please know that I recognize the risk of kicking someone out or leaving if you or the person are in a house or apartment alone—pissing off a man can come with consequences, but I am very fortunate that I haven’t run into any problems. That also comes from dating people who I know would stop if I asked them to stop.)
Now how did I learn all this? Well, as my friend Sophie said, I have a high threshold for failure. It took a lot of bad dates, bad sexual experiences, and bad partners to teach me what I like and what I deserve. I have waded through the bullshit, and, trust me, still continue to do so! It just gets easier to find the good people the more practice you have. So don’t fret if the joyful, amazing sex life doesn’t come immediately. Just like your orgasm, it takes time.
The quick: Denver is the shortest leg of my trip so far!
The dirty: Read on.
Denver, you are my second favorite city. And that’s only because nothing will ever beat Boston. This decision may be influenced by the fact that I rode a super hot dude’s face last night while high on my favorite sativa, but who’s to tell, y’all. Who’s to tell.
The funny thing about Denver is I almost skipped this leg of my trip. I was so the-opposite-of-jazzed about it that I only planned to stay the month—to go to that sex therapy and education conference and then peace out. And then, of course, every time I go into something thinking I’ll know the result, I’m always wrong.
Here’s why Denver became my second favorite leg of the trip:
#7 probably has a lot more to do with why I like Denver than I care to admit. He’s a good dude.
This is how it went down. First, let me set the scene:
Austin left me feeling completely beaten down. The men there were truly awful and the one woman I connected with turned out to be pretty emotionally unintelligent and deceitful (though the sex was great). These feelings were worsened by me leaving Hawaii because, c’mon, Hawaii was paradise and I missed it and my stupid friend HB. It’s hard to go from 11 days of laughing nonstop from the moment we woke up to the moment we went to bed in one of the most gorgeous places in the world (with zero plans or responsibilities cuz VACATION) and then move back to our respective homes thousands of miles away from each other. It was a bummer.
So when I got to Denver, I was pretty mentally exhausted, but I had some hope that dating here would be good. Because anything was better than Austin. And it is! Except for one thing.
The men here are terribly uninteresting. Have you ever swiped on a dating app and seen a man who is completely dead behind the eyes? He works an uninteresting job, has a bio that says “just ask,” wears a button-up shirt of some synthetic, striped fabric whose colors are very aesthetically displeasing, and has a haircut that’s so basic, it’s what someone off the street would draw if you instructed them to just “draw a haircut”? There’s a lot of that here.
And they all fucking hike. All of them. I have never seen so many men who believe their love of the outdoors is an adequate substitution for an actual personality.
The problem with men like this is that they don’t have passion. I try to ask “what’s your story,” and it’s like pulling teeth. There’s nothing there. It just seems like they’re climbing shit to pass the time. I would be so down if climbing shit was one of someone’s many hobbies, but that’s not the case here. A love of pizza isn’t a hobby. IPAs isn’t a hobby. Sarcasm isn’t a hobby.
And so I was like fuck it. I’m going to spend this month in Denver just focusing on myself. Like I had mentioned in my last post, I sent out a text to everyone I had been talking to on apps and said “boy bye.” And then one of those guys said he'd be happy to meet up for dinner with zero expectations if I ever changed my mind. I agreed because I was bored--and then on the day of, I almost canceled. On that first meetup, I was a giant bitch to him. Afterwards, I have no idea why he wanted to see me again. And maybe that was the point. I wanted him to hate me so that I could stick to my plan of swearing off men in Denver. If he didn’t like me, then there was no way I was going to like him. And then we could part ways.
I called him a schmoozer to his face. When he made a joke I didn’t like, I told him, he said he was sorry, and I said, “Good. You should be sorry.” I told him I thought he was trying to manipulate me into meeting up so that he could consider it a date.
But the thing is, this guy never pressured me. He was so laidback and took all the shit I was giving him in stride. Instead of getting defensive when I told him who I thought he was, he did the best thing to prove me wrong: he showed me who he is by his actions. Very sneaky, sis.
(Just kidding; that is what you should do in that kind of scenario.)
And he did. Because what he showed me was that he is a good person who had zero agenda. By the end of our first dinner, I liked him. And by the end of our second dinner, I wanted to sleep with him. I asked if he wanted to sleep with me—and very nonchalantly said it was totally cool if he didn’t and cool if he did. He said yes and then we fucked like complete animals.
Now before we get any further, I want to make one thing clear: this is NOT a “just keep trying until you convince someone to go out with you” narrative. That narrative is bullshit. He later told me that he was surprised I had asked him to fool around and that he had no plans of ever bringing it up himself. He had listened to me. When I first said no, he heard me. He never flirted or cajoled me. He treated me like a person. And him treating me like a person with a brain in her head and respecting my initial wish to not date and only be friends--that was what made me like him, NOT him convincing me. He was just himself with no ulterior motive. And I know that if I had never asked to become bed buddies, we could have spent my time in Denver hanging out as friends and it would have been just as great.
That’s how consent works. Both parties need to mutually agree that they want to act sexually together for it to work. Consent can be given and taken away at any time. And a lack of consent ultimately changing to real, enthusiastic consent (“yes please”) does not mean that the original lack of consent didn’t count. You being offered a sandwich on one day and deciding not to eat it and then getting offered that same type of sandwich a week later doesn’t mean that the first time you refused the sandwich, you didn’t really mean it.
I wanted to set that straight. And the reason I do like this person is because I know that if I said to him right now “I don’t want to be in contact anymore,” he wouldn’t ask any questions or try to fight me or say “fine” and then try to follow me on social media a bunch of times. He would respect me and not contact me again. I know this. I like this person because he respects the fuck outta my boundaries.
Good. I’m glad we’ve settled that. Because now here’s the fun stuff.
Denver friend comes up with really good date ideas. Once, we went to a bookstore and played a game. You can play this game as well: you pick a book out for the other person, and then choose a passage for them to read loud enough for other people in the bookstore to hear them. The purpose of this game is maximum discomfort. We did five rounds and chose five different genres of books. One genre was erotica (obviously), but you have no idea how embarrassing it is to read out loud how Giada de Laurentiis describes steaks, in a bookstore that's a converted theater with incredible acoustics nonetheless. Every fucking person in that bookstore heard me talk about thickness and juiciness. Well played, Denver friend. Well played.
We also decided to ask each other the famous 36 Questions to fall in love. It can get fairly intimate at times, but it's a lot less awkward than you would think. One of his answers to #25 was so good I had to write it down. The question was to make 3 "we" statements about us. "We both like," "we both seem," "we both feel," etc. For some context--he is a nonmonogamous person by choice and I am a nonmonogamous person by circumstance. We've talked about relationships (past, present, future) a fair amount. We've spoken about our independent nature and our thoughts around having an "anchor" person. When he answered question #25, he said, "We both are people who are searching, but not yearning." I loved that.
Also, there are three things that were never in my sexual repertoire: mirror play, coming from riding someone’s face (it’s a position I have a hard time orgasming in), and going to someone’s office after hours and fuckin’. I changed all of those things in Denver with this dude.
The second time I slept with my Denver friend, he bent me over the back of his bed and I realized that we were right next to the full-length mirror he uses to get ready in the morning. The visual was pretty insane and made the already hot encounter even hotter. I got a text soon afterwards that he had found another full-length mirror and he’d find a good spot for it. That spot ended up being propped up horizontally on a chest of drawers facing the bed. So while in reverse cowgirl, I could see everything from my neck down. AND IT WAS INCREDIBLE.
I know mirrors have a bit of a stigma--I'll admit I had preconceived notions that mirror play was cheesy as hell and/or vain and/or some Patrick Bateman-type shit (like when he films himself flexing while fucking two sex workers). But I’m here to tell you I was wrong. So wrong. It’s incredibly fun. We took a bunch of photos and videos because, I’m sorry, but we both looked so, so incredibly hot and this trip is all about making and collecting memories, you guys.
So after we had some mirror play, we went to dinner. Then, on the drive home, my sex friend and I talked about all the crazy places we’ve gotten down at. I get off VERY hard on sex in public places. I don’t want to ever get caught—and I haven’t—but I like being in situations where the risk of getting caught is very high. I tell him this. He’s fucked in some crazy places himself. And then he says that he started a new job recently and ahh never mind it’s a crazy idea, etc. etc. My face lights up.
No, no, we can’t.
[me absolutely beaming]
Ok we’re doing it.
[me bouncing up and down in my seat]
He turns around and we head to his office. We get past security and he gives me a tour of the place. His office is pretty high up in the building, so the view of Denver is amazing. I end up blowing him while he sits in his chair and then he eats me out while I’m lying naked on his desk. It was a blast.
My life is essentially a porno.
We ultimately make it back to his place, where we get stoned and give each other massages. For massage, I like to smoke a nice sativa-leaning hybrid because it makes me super tactile (all I want to do is touch things) without feeling tired. When I want to have stoned sex and be able to have orgasms, I take a small hit (and I mean SMALL) of some indica. The thing about hybrids and sativas (sativas more so) is that they're GREAT for massages because everything feels eye-rollingly good, but that’s the problem—your body stays at 99% the entire time and it’s hard to get to a full 100. Touch feels AMAZING, but it’s difficult to get pushed over the edge and actually come. So I don’t smoke sativa or hybrids if I want to have a ton of orgasms. Usually that sexual encounter (especially on sativa) is a lot of work towards one orgasm. It takes a while.
So we’re massaging each other and it’s so pleasureful (a word I just made up—just roll with it) that I’m like well, this guy has asked me to ride his face in the past and I never did it. The last time I rode someone’s face was, like, in 2014, because I had tried it with a few partners and it just never worked for me. But in that moment, I was like fuck it. Let’s see how this is gonna go.
The thing about this dude is I forgot how good at oral he is. I came fairly quickly and I was high on that sativa-y hybrid. This man deserves a medal.
Always believe in yourself, you guys. I leave Colorado next week (I can’t believe how quickly it flew by!) and I hope to ride this man’s face off into the sunset.
Yeah, yeah, yeah, I haven’t written about Hawaii yet. I KNOW. But guess what? I’ll be in NYC for a few weeks soon for work and will finally have the time to crank out a few blog posts about Hawaii. It’ll be worth it. Trust me.
But let’s talk about where I am now though. Denver. This is what I’m gonna say:
Denver is literal paradise.
It’s green, it’s sunny all the time, half the city is super cute and walkable (walkability is something I love about NYC and Boston) and the other half is all residential houses whose architecture I lust after, and it’s just relaxing as hell. The dispensaries are wonderful. You walk in, they scan your license, you pick out what you want, you pay, and then you're on your merry fucking way (aka HOW OBTAINING MARIJUANA IN EVERY STATE *SHOULD* BE). Everyone is chill. It was hard for me to find some good places to eat at first, but then with the guidance of a few new friends (and the dude I’m “dating” here—I mean “dating” in the sense that we go on dates together), I’ve found some good stuff. All in all, the city has good energy.
The only thing I take issue with is that it’s incredibly, painfully, noticeably white. It makes Asheville look like fuckin' Epcot, you guys.
Denver is a place I see myself visiting from time to time for vacation or whatever, but I sure as hell would never live here. Besides the lack of diversity, I had forgotten that, well, the altitude is a thing.
When I first got here, I thought I was becoming diabetic (which, if you know how I eat, wouldn’t be surprising at all to you—my food pyramid is essentially a pyramid made out of sugar cubes). I'd drink so much water but would still be constantly parched. For the first time in my life, my lips got so dry they started cracking (and, mind you, I’ve survived some pretty gnarly NY winters). I felt like shit the first week I got here. And then someone reminded me that we’re 5,000+ feet above sea level and that Denver has an incredibly dry climate.
“You never get used to it,” my Airbnb host told me. `
But anyway—I felt like I was getting sick, I felt wiped out, and then I started meeting some pretty shitty men.
As always, I encountered men that don't respect my boundaries:
Just a heads up that EVERY man who has ever harassed me has been someone who has told me they would never harass me. EVERY ONE has told me they'd respect my wishes if I decided to cut off contact. Every single fucking one of them. So a guy telling me “I would never do that” means absolutely nothing—and men should realize this before they say it. “That’s not me”? I have no fucking idea if that is indeed the case or not. So just tell me you’re sorry that it happens to me a lot and show me by your actions instead of your words that you would never do such a thing.
Then, the next guy, WHO STARTED OFF SO COOL AND KIND, randomly texted me the day before we met (guys *always* fuck it up at the 11th hour, I swear to GOD) that he was looking forward to meeting me the next day and… was feeling frisky while watching a hockey game with his friends (???) and was planning on going home to masturbate (you guys, I don’t even fucking know anymore):
Then it just came down to this, honestly:
Eventually, I figured, you know what? I’m only in Denver for a month. I don’t have to date. Why don’t I focus on some self-care? And so I did! I started reading an incredible novel (How Should A Person Be by Sheila Heti) and swimming laps on my lunch break, did things like take an hour-long walk from my place to the Denver Botanic Gardens (where I took some tincture and stared at a baby bunny eating grass for, like, an hour), and started pitching magazine articles again. I texted all the guys who I had been talking to on various apps and had given my number to: “Listen. I don’t think I’m going to date in Denver. Take care.” I was going to devote my energy towards building some friendships. Because, at the end of the day, I didn’t have the emotional energy to date, but I always love meeting new people and wanted some friends to do shit with without any sexual expectations.
And I did! I met a few really awesome women on Bumble BFF—and I know what you’re thinking. Trust me, I felt like a total weirdo going on an app to find new friends, but it is actually a fabulous tool when you move to a new place and don’t know anyone. I met someone for lunch one day to make sure we got along and the next day she recommended a place for my first tubing experience, which was so fun. I highly recommend Bumble BFF.
Next, I met a nice person on social media (ah, the modern world!) who lives in Denver and he showed me a great place to eat. [Please note that I never meet up with people from social media, especially if they're under 35 and/or single (and he was neither). So if you’re a dude reading this and are like, “I’m gonna slide into her DMs,” LOL, buddy. It ain’t gonna happen unless you’re Adam Pally.] But anyway, he, a fellow East Coaster (!) and I went out and had a great time. New friends for the win!
And then something interesting happened. Remember when I texted all the dudes I met on apps, “I’m not going to date in Denver BYE”? One of those guys reached out and said he truly only wanted to meet me because he thought I was interesting (to be fair, my OKCupid profile is incredible) and that he’s nonmonogamous with a few partners, so he truly wasn’t looking to go out solely for romantic/sexual reasons. We didn't have to go on a date. If I wanted to make another new friend, we could meet up.
I figured that if we met up and it was clear that he was manipulating me, I could tear him a new orifice. And if he was a genuine guy, I'd make a few pal. He turned out to be pretty great. After our first meetup, I conceded and said we could call it a date. Mostly because he’s really hot and charming and I really wanted to fuck him. Then we ended up going on three dates over the course of four days.
In every city, because I’m naturally monogamous and, well, exhausted as fuck as I travel, my ideal scenario has always been to meet someone and have a regular hookup until I leave. It just makes things easier (and safer). And, to my surprise, this person suggested us doing that. That he wanted to hang out with me as many times as we could before I left.
He’s also the kinda guy who opens the car door (not necessary at ALL, but adorable and appreciated), calls me pretty instead of cute (I hate when people call me cute—I’m not a puppy; I’m a grownass woman), thinks of super creative date ideas (my weakness), and, well, the sex is also incredible.
So that’s a good thing that’s going on. We both understand the situation for what it is and intend on being friends after I leave. I really lucked out.
And that's not even the best part! The main reason I even came to Denver was because I was attending the annual AASECT conference, which is a conference for sex therapists and sex educators. The first day of the conference, as I sat in the ballroom of a hotel surrounded by 700 people, I was on the verge of tears the entire time. These were people who talked about sex openly, thought of it as the most normal thing in the world, and were devoting their lives to helping people achieve healthy, amazing, joyful sex lives and preventing sexual violence. I have never felt more at home. It's hard when the rest of society views your passion as something weird or icky or uncomfortable that shouldn't be talked about. These were my people.
I attended lectures about how doctors are finding new ways to prevent STIs among women in underserved areas (that talk was by the amazing Maria Trent), vaginal rejuvenation, how to enhance pleasure for people with clitorises (Laurie Mintz is a GODDESS; buy her books), the ethics of disclosing personal details as a sex therapist, a comprehensive overview of pedophilia (one of the most interesting presentations I’ve ever seen, led by Michael Seto), the psychology of gay men’s cuckholding fetishes, intimacy on the asexual spectrum, a case study on the treatment of sexual aversion (i.e. non-asexual people who are not finding pleasure in sex), sex and cancer, empowering young women to advocate for their sexual pleasure (led by New York Times’ bestselling author on the subject, Peggy Orenstein, who is a total force of nature—I want to be her when I grow up), the taboos and myths around sex dolls, and how BDSM can help solve sexual trauma. I was in heaven, you guys. Literal heaven.
I also exchanged business cards with many, many people, had impromptu talks about my work, and made connections within the field spanning the country and beyond.
I told my friends this:
I'm digging you, Denver.
Dana Hamilton is a writer from New York City currently traveling across the United States on her own for all of 2018. Passionate about everything having to do with the body, she writes about sex, dating, relationships, body image, and eating disorder recovery. She is a frequent contributor to Playboy and her work has appeared in Cosmopolitan, Marie Claire, Teen Vogue, New York Magazine, Time Out NY, and SELF, among other publications. Before she became a freelance writer, she was an editor at two "Big Five" houses in the book publishing industry. She has also written four books (under a pseudonym) for HarperCollins and is currently working on her fifth novel. She holds a BA in writing and nutrition from New York University.
Dana Hamilton is a writer from New York City currently traveling across the United States on her own for all of 2018. Passionate about everything having to do with the body, she writes about sex, dating, relationships, body image, and eating disorder recovery. She is a frequent contributor to Playboy and her work has appeared in Cosmopolitan, Marie Claire, Teen Vogue, New York Magazine, Time Out NY, and SELF, among other publications. Before she became a freelance writer, she was an editor at two "Big Five" houses in the book publishing industry. She has also written four books (under a pseudonym) for HarperCollins and is currently working on her fifth novel. She holds a BA in writing and nutrition from New York University.